Orthogonal

Orthogonal Podcast

A show about finance, freelance and being better at both

165: The Next Chapter, Part One
This week, your boys discuss some big changes for this show. If you're interested in staying on this crazy train and you want to know what's going to be different, give this one a listen. High points include: How we've both grown and changed since this show launched 3.5 years ago. Who, specifically, we're trying to reach with our show. What we don't want to change. Links Visit https://getorthogonal.com for the latest update on where we're going and how to follow us. 👋 Get in touch Come get connected with...

163: Annual Planning - 2020
Your favorite biz bois are back with an in-depth discussion of why planning is important. This one is mostly Brett talking about himself, he realizes as he's doing these show notes. High points include: Brett spends an entire day planning instead of working; he did not use a spreadsheet. The goal of taking a day for planning; in our case, the outcome isn't a plan exactly... Brett outlines what he's going to offer people Brett's attempt to read an hour a day Quotes "I ain't about hand-crankin' nothin'." -...


162: Minimum Valuable Business (feat. Nalini Indorf Kaplan)
This week, your boys continue their discussion with very special guest, Nalini Indorf Kaplan. This time around, we get practical. Links Check out Nalini's System of Trust Nalini Indorf Kaplan Data Breaches GDPR in the EU ProtonMail Fast Mail Center for Humane Technology Buyer Beware 👋 Get in touch Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. If you have feedback or suggestions please don’t hesitate to reach out to us on Twitter at @getort...

161: Security w/ Nalini Indorf Kaplan
This week, your boys are blessed with a very special guest, Nalini Indorf Kaplan, who educates us about online security. High points include: Andrew has no idea why or how any of this works Do we care if people have our information? Brett's moving to the mountains Access isn't the issue, it's how the access is used Ease of use and security are always the trade-off Most professional services are about trust, not the service Are companies protecting themselves by gathering data? Or are they being creepy by s...


160: Professional Headspace
This week, your boys have a meandering, low-energy conversation about how to be a professional while still accepting the overwhelm ingredient in being a solo operator or small team. The real bummer is that it's hard and that there's no easy way to overcome this other than plowing through it. High points include: Compartmentalizing different tasks and areas of work to limit their impact on unrelated, adjacent stuff. Be objective about how everything is going. Brett outlines how he is attempting to create or...


159: Leverage Yourself
We discuss Brett's plans to try to leverage yourself. But sometimes the best way to leverage yourself is "people". But "people" can mean a LOT of different things. High points include: It might be time to hang it up Why Hitchhiker's Guide to the Galaxy is an Apples and Oranges problem Brett loves the Genius Distillery and hates Friends. It's all about brands and umbrellas Brett is wrong about Joint Ventures Can you joint venture without having to treat it like a "jobby job"? There is a lot of middle ground...

159: Leverage Yourself
We discuss various random things but also the ideas behind joining forces with another business. A "Joint Venture" if you will...

158: Future Investments
Andrew talked to someone about an idea that he thought was fascinating and your duo talks about it today. Can you take an angel investment in yourself? High points include: Why S-Corps save money on taxes Can you have an angel investment in yourself? Are you a blue chip stock or a small-cap? Maybe college should be an equity investment and not a debt investment How do you value a person? It won't be equitable, that's for sure What if we actually invested IN people, instead of leveraging them? Time value of...


157: Entropy Windows
This week, your favorite wonks delve into the idea of actively reducing the amount of stuff in your life (physical and otherwise). High points include: Not maintaining your systems will result in cruft, inefficiency, and decline. Everything should regularly earn its place in your life. Your business is either improving or declining—there's no "stable." Brett throws something away live. Jordan Peterson comes up and half of our listeners leave. Links Broken Window Theory (a criminology theory which Brett i...


156: The Elbow of The Deal
Brett and Andrew explore how to be more like "Steve". Getting together with others and how to set yourself up for success. The most impressive person here is the one who got all the people to show up Andrew reminisces about Chambers and Mixers If you can find a group of people who want to get up and make things happen - things will happen Dress for the job you want, not the job you have (aka Branding) Brett gets a uniform Just because I haven't solved your specific problem, doesn't mean I can't help you Al...

155: Respite In A World of Torture
Today, your boys discuss the difficulty of separating work from non-work for freelancers and entrepreneur types. Specifically, how much our work informs our identity. Specifically: The lack of abstraction between work and everything else How swings in work and productivity are far more obvious when you work for yourself How freelancers can successfully step away from their work Quotes "If today was a bad day, there's a high likelihood that tomorrow will be bad as well." -- Andrew Get in touch! Come get ...


154: Penny Wise
This week, your boys dig into the value of money, why it exists, and how to think about it differently. Also, Brett bought a new refrigerator and Andrew narrowly avoids mansplaining. Quotes "If money can solve a problem, it's not really a problem." -- Andrew Get in touch! Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. If you have feedback or suggestions please don’t hesitate to reach out to us on Twitter at @getorthogonal! 💚Leave Us A Revie...


153: Keep Moving and Get Out Of The Way
Andrew wants a new tattoo The duo revisits keeping moving AND getting out of the way Andrew signs happy birthday to Brett The IRS assumes you are an idiot or a criminal The Venn Diagram of fax machines and bitcoins has ZERO overlap If you want to create value, always have a solution Links Roderick on the Line Get in touch! Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. If you have feedback or suggestions please don’t hesitate to reach out t...

152: Too Busy With Freetime (feat. Geneva Carroll)
This week, our humble podcast gets a big shot of classy. We're joined by Andrew's mom, Geneva Carroll. On a recent episode, we were discussing our difficult it is to manage the tremendous amount of information, appointments, obligations, and general bullcrap we all encounter. Then we wondered what it was like for people back in the pre-Internet and pre-smartphone era. It's a pleasant, nostalgic walk down memory lane wherein, specifically, we discuss: Managing appointments for parents and kids, analog-style...


151: Be Okay With The Obsession
This week, your favorite boys are delving into the idea of obsession. Alcohol as the springboard surprises nobody. Brett begins yet another experiment with community-driven business, this time using Facebook. (You can check it out here if you’re interested). The overarching goal is to find one’s obsession, distill it into something atomic, then sell it. Links Godwin’s Law The Genius Distillery Off-topic Gems Andrew installs a bar in his home. Brett’s domestication continues in the form of wine club membe...

150: Schedules & Calendars For Days
We discuss High points include: Brett has 47 calendars and it's color-coded. Andrew wonders how people functioned without this infrastructure We might end up having Andrew's mom as a podcast Andrew was not aware that GMail paginates your email How Andrew and Brett manage email and tasks How important is the work you are doing? You have to accept the seasons of life Closing your sales funnel (because you are busy) is why you are busy Quotes "Would you say you, 'Can't even'?" -- Andrew Links Shawn Blanc G...


149: Hard Knock Life
Your duo discuss the school of hard knocks - is it braggy? Is it useful? Is experience better than education? We'll see! High points include: Why Andrew dislikes people who always claim to be "from the school of hard knocks" If you are a business owner, we assume you went there Adversity is a standard part of being a business owner And adversity doesn't mean you will be successful You never graduate from the school of hard knocks Quotes "Just because you started a business isn't particularly remarkable" ...

148: The Trust Game
Why asking groups is the best way to get a pretty OK idea. But not much better. We unpack why sometimes trusting authority (or experience) is more efficient. Which is why trust is so key to all aspects of business. High points include: Why democracy will never give the best answer. Assuming someone else is "in charge" is dangerous. Just because you don't like it, doesn't make it wrong Just because you like it, doesn't make it right Trust is key in all business. The more money involved, the less trust you n...

147: Outsource Everything but Your Genius
This week, your band of brothers unpacks yet another floor on the Skyscraper of Wealth™. Specifically, we talk about management through delegation. But the delegation must be trustworthy. High points include: You're not outsourcing tasks, you're freeing up mental bandwidth What management isn't How to transition from a person who does work to an actual business. Quotes "You can't do a little bit of cocaine." -- Andrew Get in touch! Come get connected with us on Spectrum the newest place to connect with ...


146: The Art of Knowing Just Enough
The Orthogonal duo today discusses how you really need to have a basic understanding of the parts of businesses. And also how being "good enough" is often good enough. If you want to get good at something, focus on the few key parts of it If you want to be a business owner you have to be "good enough" at things like accounting, marketing, finance, and management If you treat everything as"that's not my thing" - you make yourself fragile Proficiency trumps efficiency - Bruce Lee Routine solves more problem...

145: Snowball of Solutions
This week, your favorite business bois unpack the idea that we imagine things to be far more complicated than they are. From cars to business concepts, your imagination is causing you more trepidation than is probably appropriate. However, there's a cutoff where doing things yourself becomes more of a cost and less of a benefit. Listen and learn. Quotes "Assume you are smart enough." "DIY is cheaper until it isn't." -- Homie Jeremy "I'm paying for the years, not the minutes." Links A really fun XKCD joke...

145: Cognitive Spelunking
Your dynamic duo digs into what us freelancers call "cognitive spelunking". Which, in the tower of business, is the research and development portion of the tower. We talk about that means and how it is different from improving your operations and researching a market. High points include: Most people just accept things. Life might be simpler that way Cognitive Spelunking is R&D in the tower of Business Brett knows EVERYTHING. Andrew is impressed Market research is not R&D Andrew thinks R&D is testing the e...


143: A Dog Called Brisket
This week, your favorite two dorks build a lexicon for freelancers and small business types. High points include: Andrew is a man about town, but only compared to Brett Knowing your target makes marketing AND operations more efficient More efficient = more money Don't be terrified to send someone away that doesn't fit Scarcity mindset versus an abundance mindset Authentic is profitable Avatar is not just a James Cameron movie Andrew's new dog has the #1 name for Texas and #2 Worldwide Links Freelancer Le...

142: The Freelancer Lexicon
This week, your favorite two dorks build a lexicon for freelancers and small business types. High points include: How to avoid getting "freelanced" Andrew encourages Brett to workshop some of the terms discussed. Brett blanches. Brett promises something in the episode that he totally didn't do yet. Also, Andrew didn't like Brett's abbreviation, "'lanced." Links Freelancer Lexicon — work in progress l'espirit de l'escalier Get in touch! Come get connected with us on Spectrum the newest place to connect w...

141: What's Our Plan B?
This week, your boys dig into the layers of a business. We call it The Skyscraper of Wealth. High points include: There are always more opportunities than you have resources to exploit Impatience does more damage to a business than missing out does The tighter you squeeze it, the harder it is to make it happen People that are buying or selling in hurry are in a bad position Never under price liquidity - just because you have money doesn't mean that there are good investments Bonus We start our own langua...


140: Skyscraper of Wealth
This week, your boys dig into the layers of a business. We call it The Skyscraper of Wealth. High points include: How non-production work is integral to the success of a business Planning to plan A percentage-based breakout of how your time should be spent Bonus Brett got a new dog. A serious upgrade. Quotes "That's very t-shirtable." Get in touch! Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. If you have feedback or suggestions please ...

139: Pivot for Progress
Today we dig into 90-minute offer and what happened. It didn't go as planned - but isn't that just SO FREELANCER? High points include: It took more than 90 minutes to explain how to make it in 90 minutes Video production has lots of logistics, like beer and bathroom breaks Our careers are made up of a series of failed ideas But most of our success comes from setting unreasonable goals Brett is self-conscious. Shocker. Quotes "I could attribute a great deal of my personal and business success to setting un...

138: Build In Management
Using pools and sod cutters as analogies, your boys in blue unpack digging in versus outsourcing, improving your processes, and how to move grass around a yard. High points include: Deciding when to work through a complicated problem (vs giving up and hiring help) Building in time for internal improvement and refinement Why Andrew thinks everybody is a real go-getter when it comes to solving problems Thinking outside the box (like, really) Bonus Also—and this is Brett—I swore in this episode that 90minute...


137: Humans. We Introduce Bugs
Today Andrew and Brett talk about systems and automation. And how both automation and people can fail - hot tip: they fail in different ways. High points include: Brett's cat is bringing "gifts" into the house Set it and forget it is not a thing Computers systems don't degrade People love shortcuts When you streamline systems you are almost always removing double checks Brett loves checklists If clients/bosses only see the failures, it is tough to communicate value The pro of computers: They do not deviate...

136: Everyone Needs a Personal Assistant
Today we unpack why Brett is better at business (because patience) and why Andrew is not good at business (because patience). High points include: Brett has the most heartfelt sign of all time Brett likes to create lots of small insurance policies Andrew gives vague instructions and gets vague questions. Go Figure. Andrew reveals the greatest hindrance to his entire business/career Andrew needs some to police him. And his business Brett and Andrew are going to go halfsies on an admin assistant The problem ...

135: Attitude, Gratitude and Relative Success
This week, your boys unpack success relative to others, how to measure value, and scaling yourself away from the nuts and bolts of operations. High points include: Why comparing yourself to others—especially in earnings—is poison Andrew's goal for his businesses Building autonomy in team members Also, Brett and Andrew have more than enough Field Notes™ notebooks. Links 90minuteoffer.com — Brett totally meant to have this ready, but it's not. Surprise, surprise, right? But it will be soon. Get in touch! Co...


134: Leave Yourself Room To Maneuver
This week, your dynamic business duo unpack Brett's experience switching to Android after a dozen years as an iPhone user. Andrew and Brett have no sense of direction. None. The difference between rich business owner and not is process definition The best way to learn something is to teach it Brett is going to make a Wiki. Andrew isn't. Start in the middle of the spreadsheet The ability to figure things out is highly valuable Processes make it easier to identify outliers 90% of our work is dealing with exc...

133: Gamblers, Soldiers & Artists of Marketing
In this episode, your homies chat about the three types of marketers (according to a dude named David on Twitter): the Artist, the Soldier, and the Gambler. We evaluate the idea behind the categorizations and how we feel we fit into the framework. (Surprise: it's not that simple.) Links The Three Types of Marketers on Twitter Bonus Brett discusses his semi-annual evaluation of the Bullet Journal method Andrew's angry about Field Notes' boxes. Also, Brett incorrectly attributed this quote to Amarillo Sli...

132: The Thogonal's Of The Orth
This week, your dynamic business duo unpack Brett's experience switching to Android after a dozen years as an iPhone user. What Brett likes about Android What Brett doesn't like about Android Also, Brett really misses Drafts. Bonus Brett rants about how useless wearable technology is, as well as how people who use Gmail and Facebook aren't allowed to complain about privacy. Get in touch! Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. If you ...


131: Optimally Behind
This week, your biz homies discuss the idea of being perpetually behind on work, how best to deal with clients who need immediate help, and more. High points include: How to diagnose if you're actually behind in a bad way Balancing between completing current work and earning new work Planning your time so you're not behind the frickin' 8-ball all the time The secret to managing expectations of clients And, of course, a bunch more. Bonus The totally badass patch that Andrew's saintly mom made for everybod...

130: Pricing Menus
This week, we're talking about creating standard offers vs. always doing custom work as a freelancer. High points include: How to price your services News flash: people are cheap Why it's easier to do business with people you know Quotes "We have inertia to thank for a lot of things." -- Andrew Get in touch! Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. If you have feedback or suggestions please don’t hesitate to reach out to us on Twitter ...

129: The 90-Minute Business Challenge
Today we explore the idea of Brett's "90 Minute business Challenge". What is this challenge you ask? Can we take an idea, turn it into a deliverable, create the delivery and payment mechanism, create the sales copy and launch it in 90 minutes? Brett seems to think so. High points include: The requirements are: Website where the offer will live The way to buy the thing The Marketing campaign The Promotional campaign How hard is it to actually collect the money for your knowledge? Brett sends a lot of email...


128: What is Freelancing
On another special guest episode with Chris DeCaro, Andrew and Brett argue what a freelancer is. And why no definition of freelancer includes "solo-prenuer". High points include: Freelancer is a very broad term - and it changes with context People forget how different how fundamentally different being an employee and contractor are A contractor is usually a remote worker. But not all remote workers are freelancers Remote work suffers from the Jurassic Park problem Andrew doesn't believe anyone working at a...

127: Buckets of Insanity (feat. Christopher DeCaro)
On an important episode of Orthogonal Brett and Andrew discuss (with their friend Chris) the mental stresses of being a freelancer. And no one talks about it. And we should. High points include: Remote workers and freelancers - anyone working in isolation need to manage that scenario Successful freelancer have a series of tools to manage mental health and you need to be aware of that Is your "default setting" - "WORK"? Is a predisposition to anxiety correlated to a predisposition to freelancing? Is the "wo...

126: Getting Paid in Freedom
This week, your favorite business duo unpack the entrepreneur life. Specifically, how owning your own business comes with, in largely equal measure, costs as well as benefits. High points include: You have to buy the printer paper Why money isn't wealth, really. How to think about the problems you solve instead of the job for which you're best suited. Links We didn't mention this, but you should definitely watch DHH's Startup School talk because it relates directly to our point. Get in touch! Come get c...


125: Peel Away the Friction
Freelancers are almost always ahead of the tech curve. Sometimes we forget this and forget that MOST people aren't using these systems as much as we do. High points include: Brett got into tech support on accident Andrew & his wife's pillow talk mostly involves bookkeeping Does being a freelancer have to mean always having broken technology? You can get rid of eels by just closing all your accounts and seeing what breaks Right click - Combine to PDF is Andrew's secret weapon Brett needs more companies - an...

124: Tax Time 2019!
Today, Andrew unpacks several new changes to the United States tax law that entrepreneurs and freelancers will definitely want to know about. High points include: How business deductions and personal deductions are different. The most effective way to avoid paying taxes Why the new tax regulations benefit everybody other than people like us Lots and lots of important information that Brett only sorta understands. Links https://andrewcarroll.co/taxes Today's Episode Was Made Possible By Freshbooks If you...

123: Hire Because You're In Pain
Today we welcome each other back from the new year and start a discussion of how a company ends up in legacy systems, how great Brett's new business systems will be, and the difference between viewing your company as a business versus a job. High points include: Brett's Facetime baby monitor hack Brett's work with "charlie" - a computer that was a throwback Getting rid of legacy systems is almost always a significant investment There are places where DOS is still a thing Hiring people and software when par...


122: It's Only Money
In our last episode of 2018, Andrew and Brett discuss Christmas, charity, and how spoiled Andrew's kids are. We delve into why doing things for free is usually the best price. High points include: Andrew's super life hack for Christmas present shopping Brett wants to outlaw Christmas presents Andrew reveals the best investment you'll ever make There's only two prices in professional services Quotes "Please give a crap, not just money" — Brett Get in touch! Come get connected with us on Spectrum the newest...

121: Big Money, Big Decisions
This week, your dynamic duo talk about professionalism. Specifically, how professionalism translates directly into higher fees (and clients who don't mind paying them). Bonus: an update on Brett's dog. High points include: Commodity vs. high-end services How Brett accidentally wrote a really awesome proposal Anatomy of a proposal that sells The one thing you need to go from $500 to $5000 engagements Quotes "When you're doing proposals, every time is the first time. They're all different." — Andrew "I say...

120: Rinsing Off The Turkey
Andrew gets angry about flying. And entitlement. Brett attempts to calm him down and it doesn't work. We eventually make it about business. High points include: If you can't make it through a 90-minute flight without a pizza you have lots of things wrong Entitlement is far more insidious than you think What the world needs now is over apology Where do you stop your cart in the grocery store? Not being entitled means thinking ahead and beyond yourself The best business do this because it creates joy Joy is ...


119: Trade Money for Time
We talk about time tracking, dogpocalypse, billing and time in business. High points include: Andrew's horror the one time he tried time tracking Brett's dog is no longer with him. It's not dead - just somewhere else Time tracking is the same as budgeting - step one is to find out where you are now Billing by the hour means you make less money the better you get at your job Time Tracking = Business Intelligence Value is based on opportunity cost, not time Links Screen Time Andrew's Blog Uncle Brett's Boo...

118: Andrew Learns About Marketing
In this very special episode, Brett lays out exactly how he would fix Andrew's nascent info product marketing. High points include: Andrew's mistakes when launching his Personal Financial Plan DIY Kit. Brett's dead simple plan for Andrew to build a brand with video. How to create content that sells stuff. Brett's tinfoil hat theory about Buzzfeed's clickbait content. Also, a brief update on Uncle Brett's Book Club, which you should totally join. Links Andrew's Blog Brett on Facebook Uncle Brett's Book Cl...

117: Info Products & How To Do It Awesome
Launching an information product is doable by almost anyone - and it doesn't need to have a million customers. High points include: Andrew tells Brett that he told him so. Because he did. You can make a business that doesn't need to be a unicorn Having an audience makes launching a product easier, but isn't a requisite Testing demand before you build is awesome (SEE: Kickstarter) You don't have to be a top-level expert - jut helping people who are one step below you is still creating value You can start th...


116: What makes an entrepreneur?
This week, your favorite discuss what, exactly, makes an entrepreneur. High points include: Brett provides an update on Uncle Brett's Book Club Taking control of your time when you have a million ideas Getting comfortable with disappointing people Brett floats the idea of "active rest." Andrew disagrees. Why being an entrepreneur means never being satisfied. Links Uncle Brett's Book Club Get in touch! Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and li...

115: How To Charge Money To Happy People
Mismanaging expectations with clients is usually the main reason why service businesses lose money and profitability. High points include: The potty dance Did you hose yourself upfront taking on clients? Scope creep is a thing. Always a thing Have a relief valve - so that you set the expectation you might raise the fee And you'll always think it takes less than time than it does Flat fee billing is the way to go, always, but there is an inherent risk Everything takes longer than you think You'll never get ...

114: MacGyvering A Business
This week, your boys discuss how to turn things into businesses. The short answer is: just give it a shot and see what happens. And don't make problems on purpose. High points include: Brett's decision to avoid making his book group complex before it needs to be. How to use existing tools and infrastructure to create new revenue streams (or even whole businesses) Andrew wants to get sued. Brett teaches Andrew how to search for trademarks An update on Brett's new puppy Links Macgyver Uncle Brett's Book Cl...


113: Protecting Yourself as A Freelancer
This week your dynamic duo discuss the dangers of being a freelancer that many people forget about - health benefits, disability, and liability protection. Specifically, we'll discuss: Brett got a dog - we discuss his name Brett launched a business! And did math on reading - which is impressive Our social safety nets are built around the employer/employee relationship - which means freelancers don't get access to them Your salary is more than just the gross pay on your paycheck Are you saving something in ...

112: The Start of Something New
This week, your dynamic duo discuss the new business they're starting together. Instead of being all secretive and such like last time, we're going to follow sage advice and "iterate in public." Specifically, we'll discuss: Why the previous business didn't work Why this version will have a better chance of working The difference between the two offerings (and why the first one wasn't that great) The fact that this could definitely fail and why we are going to do it anyway. Why you have to consider the requ...

111: Business is Failure
This week, your boys discuss a perennial issue for self-starters: failure. Andrew has a problem with a colleague. Colleague issues criticism from the sidelines instead of getting into what President Roosevelt calls "The Arena." With this experience as a jumping-off point, we explore the idea of failure within business and dealing with critics. High points include: Brett's dismal success rate The key to surviving failure Why criticism requires credibility Other stuff: Andrew finished his holster and he al...


110: Asking All The Questions
Andrew asks Brett what he would do different when launching his business. Andrew of course chimes in. And has opinions. High points include: What can you fake and what can you NOT fake Brett talks about Mail Chimp. Again. Brett also does not PREFER Squarespace Don't be afraid to ask - successful people aren't successful because they hold others back Don't have regrets - rapidly iterate! Quote "Double your fees, lose half your clients, go home early" -Brett --Andrew ---Andrew's old boss Links Stadium Tave...

109: Mousetrap Startup
This week, your favorite duo explore the ideas discussed in Chris Guillebeau's The $100 Startup. High points include: Brett's terrible business idea Unusual paths to success The mental lines we draw around what's possible (and how to let go of limiting beliefs) The question Brett asks himself when he's afraid of something Links The $100 Startup by Chris Guillebeau Today's Episode Was Made Possible By Freshbooks If you have a business, you need to keep your books lookin' good, and Freshbooks makes it so ...

108: Time is Wealth
Your favorite homies are discussing how time and leisure are more important pursuits than money. High points include: You have to choose time to rest (and treat it as important). What will actually happen if you take a break. In terms of time, you are probably wealthier than you realize. Also, Brett tells Andrew how to poach an egg. Quotes ”Five of me couldn’t do all the crap I think of.” — Brett Links The $100 Startup by Chris Guillebeau Andrew’s homemade holster Today's Episode Was Made Possible By ...


107: Ten Pounds of Work In A Five Pound Bag
Andrew wonders how Brett randomly writes a book. Brett explains that being proactive is the key to, well everything. Also, how do you when you are doing "enough" work? It's really common to be on your back foot (being reactive) Being NOT on your back foot is definitely superior (being proactive) But it isn't always that simple... It's more simple than you think We've said it before, we'll say it again: GETTING THINGS DONE Goals versus desire - learn the difference We all need to give ourselves a little mor...

106: Flavors of CPA (feat. Jeremy - Part 2)
The continuation of our conversation with Jeremy. We chat about business scoping and how to control your business. Flexibility and responsiveness (should) increase costs Client education is important Being true to your business model is how you stay profitable People hate not knowing the price W-2s aren't as secure as you might think When a client DOES subscribe to your business, you have responsibilities to them A great business builds incentives that align the interests of owners and customers Quotes "I...

105: Flavors of CPA (feat. Jeremy - Part 1)
Today we talk about quitting your job, starting a new thing and why being a specialist is the wave of the future, but has some downsides. Jeremy tells his story of quitting his job and starting his own company Accountant does not equal CPA All professional jobs have gradients - you almost never just hire "a doctor" or "a lawyer" The new economy is creating more specialists The power of specialization - it also creates dangers Sometimes internships aren't that good at preparing you for the actual work Nothi...


104: Garage Sale Money
This week, enjoy part two of Orthogonal After Dark. (That just means we recorded this episode at night. Nothing freaky.) Brett has a garage sale and your dynamic duo discuss the business lessons contained therein. High points include: How a local real estate agent demonstrated fantastic marketing. Brett's pricing idea that fixed his "engagement problem." Brett has a mediocre business idea and still doesn't understand tax deductions. Garage sales as analogy for investments. We revisit outcome-independent th...

103: Tricked Out Chrome Extensions
In this episode, your favorite podcast duo deal with Brett's mild Crisis of Tech. Highlights include: Why Brett is wondering what an Android life would be like Andrew's recovery plan if somebody threw his phone into a well Brett offers some rare, candid criticism of Apple We discuss how the mobile hardware vs. software conversation has changed in recent years Brett's household changes cell carriers and it goes poorly Bonus: we recorded this episode (and the next one) in the evening for a change. Alcohol w...

102: Conferencing for Dummies (feat. Ryan McRae)
Today Brett is joined again by the indomitable Ryan McRae, the ADHD Nerd. They have a great conversation about fitting reading in, finding a great junk book, and conferences. You might be surprised how much time you have to read during the day But to be a well-read person, you have to make it happen "Junk books" can still be productive Brett revisits his hate of conferences Ryan's patented, never fail system for attending a conference. Especially if you hate them. Conferences are for making friends, not de...


101: Buying Back Time (feat. Ryan McRae)
Today Brett is joined by the infamous Ryan McRae, the ADHD Nerd. Andrew is someplace. Ryan looked up Orthogonal! A great conversation ensues about how Brett and Ryan got started in online sales, their experiences and the weird feeling of people buying your stuff. Just sell the muffin. Some people still don't understand that you can make money on the internet Building a list is always a slow slog Balancing all the parts of an online business often resembles WORK "Get up and Hustle" sounds easy, but buildin...

100: The Strenuous Life Badge
Your dynamic duo discusses Andrew's new project - and how challenging yourself makes all the difference in life. A BIG THANK YOU TO THE ALL OF YOU WONDERFUL LISTENERS WHO HAVE SPENT 100 EPISODES LISTENING TO US RAMBLE. WE LOVE YOU. We are really glad that we have this podcast to "stay in touch" Brett reminds Andrew that sometimes he loves hard The math says you should do nothing but your thing - but is that true? Brett fixed his own stove - Andrew has no idea what to do with his fence Sometimes structure m...

99: Ego Is The Enemy & Goats Are Just The Best
Brett is now married. Andrew and his family flew out from Texas to attend the wedding. All good things. Today, your favorite duo discuss Brett getting excited about barbecues, how he's dealing with an outsized amount of garbage, and Ryan Holiday's fantastic book, Ego is the Enemy. Links Ego is the Enemy by Ryan Holiday Get in touch! Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. If you have feedback or suggestions please don’t hesitate to re...


98: Business Party Hats (feat. Kathy Campbell)
This week, Brett is on his honeymoon after successfully marrying his wife. In his stead, friend of the show Kathy Campbell—The Unicorn Sidekick—joins Andrew to discuss small business, life, and sundry other topics. Topics How angry Brett would be if Andrew announced his phone number on the podcast The return of the conehead? Are we dunces for being small business owners? Product businesses vs. client businesses How to treat your clients when starting your business Parenting and working from home Kathy expl...

technology business finance marketing web

97: Curiosity And Idea Bone Saws
Last week we talked about putting ideas out of the misery. But what happens if an idea is still good enough to keep around, but isn't good enough to be the main focus? What you need is a bone saw, not an idea pistol. Highlights include: Sometimes things are more nuanced than "alive" or "behind the barn" What's the math behind keeping a business at Minimum Viable Momentum (tm) (c) Dispassionate analysis is the key Focusing on one thing will make it more successful, but can be more dangerous Diversifying yo...

marketing business technology finance web

96: Holster The Idea Pistol
Brett and Andrew explore what it means to keep a project going and why that is important. Also, things get dark. A lot of discussion of putting animals down. Highlights include: The difference between murder, assassinate, excise and euthanize - things get weird Retail investors versus institutional investors - the difference is emotional decision making When the love of the idea keeps the zombies moving Sometimes killing the idea is the best idea you'll never do Brett doesn't have his bar. He is feeling un...

technology finance web business marketing


95: Minimum Viable Momentum (MVM)
Brett and Andrew explore what it means to keep a project going and why that is important. Also, things get dark. A lot of discussion of putting animals down. Highlights include: Why killing projects getting more done. Your emotional investment in your ideas is likely holding you back It is better to cycle quickly through lots of ideas than hold onto mediocre ones Just because you can do business with someone doesn't mean you are going to The good news is that in the modern world there are more opportnities...

marketing business technology finance web

94: Keep It Rolling
Andrew makes Brett watch a youtube video about Will Smith. They extrapolate how to be successful from it. It is smarter than it sounds. Highlights include: "Be where people is doing it!" "Take ten minutes, right now, and change your life forever" Two stories with the same decision/result 140 years apart - technology has nothing to do with success Never underestimate the power of forward momentum Bonus: Quotes "'NO PARALYSIS, DO ANALYSIS'" -Quincy Jones, allegedly Links How I Became the Fresh Prince How t...

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93: Workflow Interruption Org-Charts
Andrew has turned into a hermit like Brett and Brett is now going out to offices. Black is white, up is down, and are you allowed to interrupt your coworkers? Highlights include: Sometimes moving vans don't show up How much coworking is actually going on? Do knowledge workers need less collaboration than people think? There is a benefit to being around other humans, but it might not be getting more work done Interruption goes two ways - the person whose workflow was interrupted and the person who needs the...

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92: RE-AIR Ep. 20 - Website Office Lobby
Today's episode is all about workspaces. Specifically... What does a workspace say about company culture? Does physical space create legitimacy?  How does your digital presence replicate the physical space? What affect does physical space have on your work? Also, Brett and Andrew are too clever for their own good. Come chat with us in our Spectrum Channel! Join other listeners and ask us any questions you have about today's episode, finance, freelance, business, marketing, you name it! Show Notes: Brett ...

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91: RE-AIR Ep. 1 - Pin Needle Freelance
We talk about the difficulty of defining our jobs and Andrew attempts to explain why we are becoming so much more specialized with economics. We discuss how this drives the move towards Freelance work and the trials and tribulations that come from that. Does not having a job make you more wealthy? Come chat with us in our Spectrum Channel! Join other listeners and ask us any questions you have about today's episode, finance, freelance, business, marketing, you name it! Show Notes: Brett on Twitter Andrew o...

freelance technology business finance marketing

90: Investment vs. Cost
In the last LIVE epiosde (until Andrew is back in town and they do a live episode again) Andrew and Brett talk about weddings playlists, moving plans and the difference between investments and costs. Highlights include: Brett doesn't know what investment vs. cost means Andrew's movin' to Texas! Cutting costs can hurt your business Fix your business before cutting costs Oursourcing your genius Quotes "You're stepping over dollars to pick up pennies" Links Operation Moneysuck Today's Episode Was Made Possib...

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89: When Business Systems Actually Work
In their second to last LIVE episode (until Andrew is back in town and they do a live episode again) your dynamic duo discuss how great it is when business systems work - and why that's the goal of every business. Highlights include: Brett doesn't know how math works Their plan to record Orthogonal and have a YOUTUBE channel as well There are lots of ways to relieve stress - but the best kind is knowing you built the systems that fix things Businesses are a collection of systems one which leads to another ...

management freelance technology business finance marketing web

88: The Puck Stops Here
Andrew & Brett spend this episode talking about the pros and cons of hiring people. Let's be honest, it's mostly Andrew listing the cons. Most people don't care as much as you do - which is easy to forget But business owners need to remember that you can't pay employees in "vision" Autonomy and responsibility are positively correlated (That means they go hand in hand) The trouble with staff is it can add extra layers of frustration Quotes "The benefit of being an employee is that you get to say "No" Links...

87: Poopy Diaper Business Time
Brett and Andrew spend a lot of time talking about kids (unsurprising) and how like running a business they can be. There is a lot of time spent doing things that you don't want to do. Central time will be a competitive advantage for Andrew Changing diapers is a humbling experience - you should try it! Being a business owner means doing lots of things you don't want to do What you "want" to do is not a relevant factor in many business decisions Delegating is key to business - but sometimes you have to shav...


86: Margins of Stress
Andrew and Brett are tired all the time. It has a lot to do with stress. Having children means you are tired forever "Make time for it" is not a helpful answer and creating margin is more complicated than that sounds The unique aspects of "margin" and being a business owner Not having margin in the short-run might be a necessary evil Allowing yourself some slack (or grace) is key Quotes "Well, people don't like you. People LIKE me." Links A Conference Call in Real Life on YouTube Email in Real Life on Y...

85: Dear, Google
It's a sad day, Orthogonal listeners. Andrew's moving to frickin' Texas. We discuss this and Brett fights back the tears. Second, Andrew's data is spread out across a zillion accounts, services, and systems. It's making him a little crazy, so we unpack this problem and explore possible solutions. Also, Andrew's sick of Evernote's clipping capabilities being... less than capable. You'll never believe how Brett responds... Quotes "If you're considering emailing something to yourself, your system is broken." L...

84: Branding & What it Actually Means w/ Bethany & Melinda (Part 2)
Part two of our lively chat with Bethany and Melinda! This week, we dig further into the nuts and bolts of branding, running and growing a small business. High points include: Andrew’s mic-drop-worthy point about scale vs. scope The importance of having a good network of contractors (and why you should fire bad ones) Why Andrew has multiple businesses and multiple brands based around one core competency The business reason for Andrew’s move to Texas. Brett is getting business cards and isn’t happy about i...


83: Branding & What it Actually Means w/ Bethany & Melinda
Andrew and Brett are joined by friends of the show Melinda and Bethany - we talk branding and business. This is part one of two! High points include: How moving from freelance to being a business owner is great But moving from a business to a brand is even BETTER What does all this mean? The challenge of turning a business into a brand Bonus Brett would like some whiskey Links Melinda Livsey` Bethany Michaels Trello Check out Toolsday on Spec.FM! Today's Episode Was Made Possible Thanks to: Vast...

82: Brett Gets Google Productive
Andrew introduces his new homey and Brett talks about Google. Also, hot dogs. High points include: Why using something like Freshbooks will make Andrew so, so very happy Turns out, when you have to interact with people, technology gets trickier Sometimes things just have to WORK You get what you pay for Also, ads are sometimes useful because, you know, you might want the thing Andrew's Robe Goldberg machine of email service Brett & Andrew launch Irreverant Monk Bonus New friend of the show, Jeremy Wells L...

81: Side Hustle to Full Time Gig & When To Make It Official (feat. Ryan Irelan)
With Andrew out, we have decent, cohesive content for once! Welcome our guest, Ryan Irelan. High points include: Why side gig to full-time is a great way to start The secret to starting - don't do it when your expenses are high Jobs have a lot more tentacles than you realize You might be afraid, but whatever the challenge you'll figure it out The less stuff - needs less money - means less stuff snowball to a more simple life Bonus We learn that Thundersnow is a real thing. Links Thanks to Freshbooks for...


80: Uber, but for Cilantro
This week, your dynamic duo discuss pivoting business ideas. In particular, Brett describes how he's shifting a hair-brained affiliate marketing idea into a service business. Bigger points include: When to pivot an idea (or, how to know if your current implementation isn't working) How big a market has to be in order to support a profitable business Locate the problem before you create the solution. The websites you should look Bonus Brett got engaged! This is good. More to come on that front as the situa...

79: Go Union!
The boys discuss the what a Freelancer "union" might look like and why you might want one. Seems unlikely they will start it though. But we'd love to help! High points: The downfalls of working freelance How working as a group might be helpful Definitely no meetings Knowing more about your industry helps you not get screwed We're a union, but one that tells you how to do things Standards can be helpful Bonus: Disneyland is pretty awesome Links Thanks to Freshbooks for sponsoring the show Check out Toolsd...

78: Profit First Part Deux (feat. Christopher DeCaro)
Turns out there are lots of kinds of businesses. And thinking about it in a business-like manner is a great start to being successful - no matter HOW many bank accounts you have. High points: Chris can't countenance not having profit in a business The single most valuable page in the book (it's worth the whole cost of the book) Andrew explains how to do Profit First without bank accounts Things being hard is not an excuse to not run your business properly Maybe everyone shouldn't be a business owner Being ...


77: Working Well With Others
People. The key to all business - Both good and bad! Turns out, people are different and complicated. High points: Andrew's kids are secretly trying to make him go insane The different forms of motivation Independent folks still want parameters Habits versus systems Why freelancers REALLY need to understand this - it isn't just employees Levels of maturity - dependent, independent, and interdependence Bonus: We give our opinions on the Mile High City - Denver. Brett thinks High St is hilarious. Links Che...

76: Choosing Your Technology Ecosystem
The dynamic duo is back in your ears once again. This time, we discuss the current crop of voice-enabled robots and the ecosystems they represent. High points: Why Brett thinks Siri sucks compared to Alexa Andrew uses Amazon for pretty much everything How Amazon makes it simple to have lots of Echo devices Why Brett and Andrew are both perfectly content with having Amazon hear every word they say while at home Bonus: While Brett was writing these show notes, his Echo Dot did not. shut. up. Links Amazon E...

75: Economics As Pie
This week, your boys discuss Brett’s current read: Economics in One Lesson by Henry Hazlitt. Specifically, Andrew—who actually knows about economics—helps Brett unpack the concepts laid out in the book. Despite being 70 years old, the book describes some fairly timeless principles. Brett has mixed success in understanding them. High points: Moral vs economic problems The problem of assigning businesses the task of solving societies ills Creating jobs vs increasing worker productivity Bonus: Brett says “ta...


74: Bread and Fairness
As a public service, Andrew and Brett set out to dispel the business myth that you should succeed simply because you tried. High points: Brett gets a little ranty about how success and wealth are sold as paint-by-numbers processes. Andrew enumerates the reason most businesses fail. Why our default assumptions about business are skewed. Your best chances are success are based on your willingness to take risks and try new things. Related: people are bad at evaluating risk. Bonus: We take a rather long detou...

73: Andrew Shreds Profit First
Brett's friend Chris Johnson recommended that he read a book called Profit First by Mike Michalowicz. In a nut, it's a simple guide to taking the revenue of your business and creating an easy way to gauge business health and control how revenue is distributed. Thing is, Andrew kinda hates this book (he hasn't read it, but still). He doesn't actually hate the book, but he doesn't think it solves a new problem. High points include: Andrew explains the financial principles on which the author is basing is met...

72: Leadership w/ Dave Stachowiak - Pt 2
This week we continue the conversation including topics like: How leadership and personal productivity coincide. Why mentors, peers, and someone to talk to is an important leadership skill Leadership is empowering and motivating yourself just as much as empowering and motivating others Creating margin for the space to be creative and thinking about leadership Quotes "A leader is best when people barely know he exists when his work is done, his aim fulfilled they will say we did it ourselves. -- Lao Tzu "...


71: Leadership w/ Dave Stachowiak - Pt 1
What is a leader? Who is a leader? Why is leadership is important? Also, Brett is TOTALLY a leader. High points: Dave is an amazing sport to put up with and Brett's kids Dave is a podcast hipster (he's been listening to them since before it was cool!) Great producers are often lousy leaders - they turn into micromanagers Leadership skills have nothing to do with your job or your level in the organization Great story about a navy ship going from being the worst to the best just by changing language It is OK...

70: Andrew Knows His Hardware
Andrew and Brett talk about hardware and how/where to buy it. Plus a brief interlude of movies. High points: Andrew explains how he buys Surface hardware (hint, it is the cheaper way) Andrew's teams continued issues with peripherals. Is this just how people work? Sometimes if you force your workflow into the tools, you'll be faster Andrew is in love with Asana except for this one weird feature IT DOESN'T HAVE An IPad pro mounted in a case with a keyboard is the same as a Surface Pro - Why can't we all just...

69: More Words
Brett and Andrew discuss why and how to hire an advisor. How to ask good questions of them and how to make sure you have the support you need. High points: Don't hire an advisor, if all you need is basics. Why Brett hires advisors more than a lot of people do Why relationships are with advisors or anyone else, is critical, even in our virtual world Why networking is lame and there is no shortcut to relational capital Andrew tries to hire Brett to teach everyone he knows how to ask questions Quotes "I nee...


68: Brett Doesn't Do Conferences
Brett and Andrew discuss Andrew's talk at the Release Notes conference in Chicago. How to do conferences correctly and why Brett absolutely hates them. High points: Which of Andrew's presentation jokes worked and which didn't Brett and Andrew's experience at WWDC. How long it takes Brett to forget that he hates conferences and fish and chips. Andrew suggests "OrthogonalCon" and Brett imposes several rules that basically make it not a conference at all. Quotes "Everybody hates accountants. Accountants hat...

67: Pricing Is Hard
Andrew has a new information product and he needs to figure out how to price it. He tries economics and it turns out it doesn't always work as well in practice as it does in theory. Highlights cover: Products (physical, digital) are harder to price than services? We circle back to price elasticity Brett's super simple plan to test is..... to just test Start small and building up is the best Andrew reveals just how little he knows about how most things in his world work Imposter syndrome is real and happens...

66: Less Spin The Wheel, More Focus
This week, your favorite business duo are talking about planning and how plans bring happiness. Specifically, Andrew talks about his presentation at the Release Notes conference in Chicago. We recorded this episode before he gave the talk, but this episode will air after he's done. It's weird. High points include: Andrew talking about how much more reading he gets done with his #multiphonelyfe How Kindles make reading an event and the phone not so much The benefit to recreating the division between "home p...


65: Happiness Is Faith In The Plan
This week, your favorite business duo are talking about planning and how plans bring happiness. Specifically, Andrew talks about his presentation at the Release Notes conference in Chicago. We recorded this episode before he gave the talk, but this episode will air after he's done. It's weird. High points include: Andrew gets disk images from Apple computers and has no clue what to do with them. Andrew decides to actually prepare for his talk instead of his usual strategy of not preparing anything. How lac...

64: Goals vs. Systems
This week, your boys in bidniss are talking about a subject near and dear to Brett's heart: goals vs. systems. Specifically, how system-based thinking can unintuitively do more to help you achieve your goals than goal-based thinking can. Highlights include: How to make time each day for just about anything The main reason why you're not able to move forward with what's important to you Links How to Fail at Almost Everything (And Still Win Big) by Scott Adams The First 20 Hours by Josh Kaufman Getting Thi...

63: Multiple Income Streams & Donut Shops (feat. Chris DeCaro)
What qualifies as multiple income streams, why you should have them, and how to create them: Thoughts include: Does everyone hate consultants? What qualifies as multiple incomes streams? Just splitting entities doesn't count Vertical integration as a method of diversifying Andrew gets all his best business ideas from television shows Donut shops are good business Divesfying your labor is a bad idea - diversifying your investments is a great idea Bonus Chris's foolproof diet strategy is unfrosted pop tarts...


62: Fake It Till You Make It - Rinse and Repeat
Brett and Andrew dive into what exactly faking it until you make it actually means. Hint: it isn't "commit fraud". Thoughts include: You need to have a domain level understanding to actually fake things Literally no one has any idea what they are doing The actual trick is to only fake it until you get into the level, then you have to master it Don't fake a level above what you have mastered the one you're on Brett explains that leveling up doesn't necessarily mean losing clients Don't be the JV guy who sti...

61: Want To Make Money? Be an A-Hole
Your dynamic duo get back to their roots and talk some real business talk. How we make a business run, how we know if we are making enough and understanding how a real business is run. Thoughts include: The big difference between profit, savings, and living expenses How you should actually run the math of your business - is it profitable enough? Why cutting expenses (fixed expenses, at least) is a dumb way to make money The secret to infinite returns in your business How to maximize revenue in your busines...

60: Computer Smarts
Brett finally makes Andrew understand this is bad radio, but Andrew learns a LOT about programming. Turns out (tm) it isn't easy! But the bigger point is that gathering data is MUCH harder than doing work - which is an important thing to remember in business. High points include: Brett may actually be an evil hacker Filtering data is so much harder to code than you think And you do so much filtering automatically in your life than you think Computers are simultaneously smarter and dumber than humans Mayb...


59: Death to Voicemail
Andrew got a second phone and immediately broke his other phone. High points include: How a new phone turned Andrew into an annoying informed person Breaking the habit of constant feedback Andrew is a prima donna about his cables and phones Bonus Brett's birthday is NOW! Say happy birthday! Get in touch! Check us out on iTunes Come get connected with us on Spectrum the newest place to connect with your favorite Spec hosts and listeners. You can also chat with us in our Slack team! To join our team visit ...

58: Steady Hum of Vacation Anxiety
Brett went on vacation recently and did zero work. This caused him some anxiety and made vacation more difficult. This week, your boys talk about the challenges of unplugging while on vacation. High points include: The inescapable truth of vacation when you work for yourself The reality of leaving your business unattended for short periods Working with a "skeletal" set of tools that you can use from anywhere Thinking realistically about the problems that may occur when you're away Oodles more goodies Bonu...

57: Shelf of Plan Bs
Your dynamic duo discusses planning, creativity, and approaching problems: Plans are an iterative process that always need to be updated Making fully informed decisions are usually a rabbit hole you'll never escape from Constantly trying to fine tune is just scaling a problem Give a minute of thought to all the things that might happen Andrew talks about his giant baby Having a shelf of Plan Bs is the key to success. Also, Field Notes discussions. "Plans are useless, planning is indispensable" - Dwight Ei...


56: Coffeeless Code Headaches
A fun episode where Andrew tries to code and Brett tries to stop him. Highlights include: Andrew's new Surface Book's key travel (Brett criticizes manual keyboards) Andrew learns a surprising amount of information about programming (Brett overestimates Andrew's knowledge) Brett switches topics to him giving up coffee (Andrew designs a science experiment using Brett's health) We narrowly escape a pranks arms-race to the bottom Andrew figures out that you can automate programming with a powerful enough proce...

55: From Brick Layer To Grand Planner (feat. Melinda Livsey)
This week, your dynamic duo finally settle the freelancer versus business owner definition. And we, obviously, needed help. How industry looks at freelancers versus a "studio" Brick layers versus problem solvers How mindset drives more money Brett soaks in being right Additional tidbits: The biggest change to being a business owner is more MONEY Self-employed does not mean a freelancer The difference between a million dollar contract and grunt work is branding Freelancers are hired on a commodity basis B...

54: Step Away
This week, your boys chat about: Separating work from the rest of life (and how difficult it can be) Andrew mentally explores living a two-phone lifestyle The details of Andrew's web application that will automate part of his job (and generate leads for him) Additional tidbits: Remembering that we chose this work and that we're responsible for the knock on effects as well as the freedoms. Developing the habit of stepping away from work, regardless of what "must" be done—and trusting that you've done enou...


53: Think Like A Rich Person
Andrew has returned from paternity leave! He was missed. Today, your dynamic duo are discussing abundance mindset vs. scarcity mindset. Or, as Andrew calls it, thinking like a rich person (abundance) versus thinking like a poor person (scarcity). In other words, "playing to win instead of playing to not lose." This has many applications to business as well as life. High points in this episode include: How many rich people Andrew knows who are trapped in a scarcity mindset How knowledge informs our attitude...

52: Kiss The Dog Yelp Reviews (feat. Jonathan Kelly)
This week, Andrew's paternity leave continues and Brett is joined by his brother Jon—proprietor of Olde Tyme Tattoo in Fullerton, California. Brett and Jon discuss what it's like to run unorthodox businesses, how to grow your business by focusing on product excellence, and how cultural changes have made certain types of businesses easier to start and run. Other tidbits include: How Jon got creative (and slightly illegal) with his early marketing efforts Building anticipation in your future customers Brett ...

51: R.I.P Uncle Squirrel (feat. Jonathan Kelly)
Andrew is on a break this week, and Brett talks to his brother Jonathan Kelly of Olde Tyme Tattoo fame. They talk about running a tattoo shop and why culture and strategy matter. We hear about Jon's journey of opening his own shop. In particular: The pride of paying the bills The slow/busy cycles both by season and during the month Tattoos CAN have a practical purpose Doing good work is the best business model, even in tattoos Bonus "People and their millions of reasons" - Jon Kelly Thanks to our sponsor...


50: Paying To Climb Walls (feat. Natassia)
This week, your dynamic duo are back with our special guest and fellow entrepreneur, Natassia. Much of the episode involves dealing with the problems associated with business growth. And, honestly, more than a little discussion of Tony Robbins. In particular: The dangers of sub-optimal revenue Deciding to stay small as a business Figuring out what your goals are in business and what the trade-offs are Natassia's current business challenges regarding growth Investing in yourself as a means of business growt...

49: Jumping The Corporate Titanic (feat. Natassia & Bethany)
It is a veritable party o' freelancers this week. Even though our guest isn't a freelancer, she is a small business owner. We talk with Natasha about how her former bosses tried to screw her over. And how she decided to put the work in on her own and has KILLED it. Real businesses start with a calling - even boring construction ones. Why someone telling you that you won't succeed because you have no experience (or are a woman!) is horse crap - also, F#%$ that guy Andrew creates another hashtag #scorpses We...

48: Task Rabbits of Sales
Your favorite business boos are talking sales this week. Specifically, selling services vs. products. High points include: Andrew's sales strategy for landing clients contrasted with Brett's for landing new customers Identifying the pain your prospect is experiencing Brett's pricing strategy (and how he screwed it up in the past) Andrew's "anti-sale" technique for closing new clients Bonus Yet another Glengarry Glen Ross reference! Also, Jim Camp's book, Start with No. Get in touch! Come get connected wit...


47: Someday is Never (feat. Bethany Michaels)
This week, your dynamic duo welcome Bethany Michaels, a freelance social media manager from their home town. During our lively chat, we discuss challenges of running your own business including: Knowing when to say "yes" vs. "no." Making time to manage the backend processes that run your business The most surprising thing Bethany experienced when she started her business (which you'll probably recognize, if you're a business owner) How to kill a business (and a business entity, if you have one) Additional...

46: Unicorn Eyeroll
Brett begins to change his mind regarding taking on investment for his new business venture while Andrew continues attempting to convince him to do so. Andrew outlines the regulations and practices surrounding getting investment for your small business, and the steps involved in doing so, including: How to approach potential investors (and what you need when you do) How investors can get paid when your business makes money What the heck a "preferred share" is and why it sweetens the deal for the investor ...

45: Paperbacks & Dog Ears
This week, Andrew continues on his rant about the Profit. He really wants to know how the back end of that business works: The dichotomy of Hiring stellar people is how you build a business but Stellar people don't want to stick around because they are, well, stellar Brett and Andrew have very different ways of approaching hiring and growing businesses. Andrew tells the same exact story again. We dig into each of these aspects of Brett's new business and figure out what the potential problems are. Also, B...


44: Buckets of Ideas
This week, your boys on the ground discuss Brett's newest—nascent—venture and Andrew douses said idea in wisdom from NBC's reality hit, The Profit. Specifically, there are three components that dictate the success or failure of a business: People Product Process We dig into each of these aspects of Brett's new business and figure out what the potential problems are. Also, Brett repeatedly gets ahead of what Andrew wants to talk about and Andrew becomes audibly annoyed. Bonus: Brett's daughter calls him vi...

43: Icing On The Paincake
Today we talk about how people conflate the idea of family and business. How emotions get tied up in business and how that causes problems. And how people attempting to bring emotion or causes into business tend to do more harm than good. Points include: If it was fun they wouldn't pay you to do it We talk about how to bifurcate the art/social/charity and business Single-purpose tools are more efficient than multi-purpose Someone get Andrew a billion dollars and he will give you free tax services for life ...

42: Dreaming The Wrong Dreams
Some people should just not be a business owner. Points include: The opportunity to be a business owner is not the same as the right to being a business owner. More businesses are successful because of luck than any other reason Brett helps Andrew crush dreams gently and with feeling Financials are the lifeblood of a business Bonus Features We plug Olde Tyme Tattoo, where we got our awesome tattoos! "Any business owner who doesn't occasionally feel like a fraud is lying or an idiot" -- Andrew Links Ont...


41: Buff Qualifications
This week, the dynamic duo discuss how the approach reading books and implementing the knowledge in them. Andrew is pretty sure that everyone is fooling themselves into thinking that reading lots of books makes them smarter. Interesting tidbits include: Andrew has never been cranked to eleven. Ever. Not even once ever. Also, he is VERY humble. Brett explains his strategy ever for being a voracious reader and crushes Andrew's dreams Why you should spread out the topics you read about Andrew explains what is...

40: Smart Pounds
This week, the dynamic duo are talking about the guts of getting paid. Specifically, the anatomy of the get-money-from-customers-to-your-bank-account robot. Interesting tidbits include: The difference between a payment processor and a point of sale system Why you would choose a given option over others, depending on your needs How things like Square and PayPal stack up vs. traditional merchant tools Challenges and details you'll likely face when selling things, especially online Brett's horror story about ...

39: Morass of Maybe
This week, your brothers in arms unpack how to stay productive under a “hail of bullets:” somebody or some organization rips the rug out from under you and you’re suddenly scrambling. Finer points include: Why unexpected emergencies can be good for you and provide you with unique opportunities Why times of so-called “peace” can be a great deal harder (a situation Andrew eloquently called a “morass of maybes”) Andrew’s story of how his business was torn to pieces by Quickbooks Online How Brett had to—in a v...


38: Brainstorms and Such
First time in the new studio! We discuss noise and distractions and the decisions that lead to productivity increases or decreases. Also, Andrew harasses Brett. We apologize to Sarah. And we send her flowers. Brett is not very noisy. Andrew is very noisy. Andrew's very simple and replicable process for guaranteed productivity. Or not. Does reducing noise lower the of the output because of a lack of new ideas? Brett gives Andrew a super life hack Andrew wants to wake up early on an intergalactic space vesse...

37: Web Design & Quilting (feat. Shawn Blanc)
First things first. We apologize for the audio quality. Normally, it's just the two of us talking into our fancy, Spec-provided microphones. This time, we had a (remote) guest that required an astonishing about of technological duct tape to get working. As a result, both Brett and our guest Shawn sound like they're both drunk and doing their best Barry White impressions. Andrew sounds great, though, so that's good. Our bad. All will be well next week! Anyway... This week, your boys are honored to welcome fr...

36: Knowledge on Knowledge
The differences between skill acquisition and knowledge acquisition. A too long discussion about drones and the mall Andrew learns to be a programmer, but not really Brett discusses his journey into learning self-discipline How you can make money with skills and no knowledge Andrew's gives out a free business model Bonus quote: " When you shrink your market you increase your margins" -- Andrew The First 20 Hours Get in touch! Come chat with us in our Slack team! Over 5,000 designers and developers have ...


35: Work/Life Liturgy
Andrew launches into a metaphor using churches, ritual and the power of habit. Andrew explains the difference between procurement and buying and Brett (briefly) explains why/how the stand/sit/kneel church operates Why rituals force you into proactive versus reactive mode How to best manage the cycles of launching and maintaining projects How to make sure that "someday" isn't never You can't do everything you want - and you'll be more successful when you realize that Bonus quote: "Someday is less prickly ...

34: Manageable Ramifications
This week, the dynamic duo talk more about how to locate the information needed to alleviate the uncertainty we touched on last week. Also, How Brett's running of his business frustrates Andrew Andrew's secret weapon (a high risk tolerance) Playing to win vs. playing to not lose How more data is available to us today than in the past Brett tortures a car analogy Bonus quote: "Any portmanteau that ends in 'preneur' is French for 'slap me in the mouth'." -- Brett Kelly Get in touch! Come chat with us in o...

33: Choose Your Own Emergency
This week, your homeboys are talking about anxiety. Where does anxiety come from? What causes it and what can we do to alleviate it? Reducing anxiety means reducing uncertainty. Uncertainty comes from a lack of information. Salient points include: Anxiety isn't a necessary evil However, it tends to compound when left unchecked Brett's current anxious situation Andrew's way of alleviating Brett's anxiety without actually solving the problem How differing attitudes toward money can create anxiety (or not) An...


32: No Money, No Problems
This action-packed episode begins with several minutes of Andrew recounting his visit to the Field Notes Brand store in Chicago. Brett and Andrew are both fans. Skip to the 5:30 mark if you don't care about that. After that, your boys dig deep into the current landscape of productivity tools. Andrew drools on his Surface Pro and Brett sneers condescendingly from behind his iPad Pro. Also: How different platform providers are trying to lock you in Brett squawks about the quality of third-party Windows softw...

31: Rent a Brain
Sending out an RFP everytime you need help isn't efficient. How do you build a go-to list of people that can help you: Brett impresses everyone with his SAT words Why billing your network is the best idea, but billing your friends is lame Why building a network focused on your business helps you be more efficient to your friends Knowing where to hit the pipe is the most valuable part of being a plumber and you shouldn't let anyone buy you a beer Andrew invents another business, if anyone wants to help - pl...

30: Stress Level Coin Toss
As a quasi follow-up to last week we dig down into stress a little more. We chat about: Where and how stress manifests and monopolizes your attention Andrew's super great, never fails, best way to deal with stress (or whatever) Working through stress can actually create more work Andrew isn't any good at actually doing work But what happens when the solution to stress causes more stress? Always do sober what you say you're going to do drunk. That'll teach you to keep your mouth shut. Links: https://www.be...


29: Hover Car Market Share
This week, your boys talk about two of the more problematic aspects of running your own business: uncertainty and stress. Specifically: Understanding the causes of uncertainty in new businesses, products, or initiatives How Andrew designs businesses to reduce the risk of failure (and virtually eliminate uncertainty) Separating imposter syndrome from uncertainty Why Brett loves doing the dishes The real lesson you learn when you fail at something Also, Brett comes up with a pretty great bar-related product...

28: Irreverent Monk
Ahhh, Just In Time Inventory. Pretty sure that's an official term of some kind, so I'm capitalizing it. We don't have to wait for really anything these days. Listen to Andrew and I talk about the agony and the ecstasy of living a life facilitated largely by Amazon and Google. This one is longer than normal, but it's worth it. Get in touch! Come chat with us in our Slack team! Over 5,000 designers and developers have already joined our team, chatting about the latest tools and news in the design world. To jo...

27: Living With Cooties + Deep Work (feat. Christopher DeCaro)
We launch this week the Orthogonal book club, discussing with Chris DeCaro the book Deep Work: Why dust jackets are the devil We all pretty much agree being that being sensitive a daffodil is not cool Why not everyone gets to do deep work Why professionals have inspiration strike every day at 9am Andrew examines the economics of sword making Links Kneadle Christopher DeCaro on Twitter Get in touch! Come chat with us in our Slack team! Over 5,000 designers and developers have already joined our team, chatt...


26: Stale Water Styrofoam (feat. Christopher DeCaro)
This week, your boys conduct a hard-hitting interview with designer, developer, and business owner Christopher "Fire Beard" DeCaro of Kneadle. Topics discussed include: The value of education in pursuing a design career A list of things Brett and Andrew do that annoy Christopher Why Christopher hates our podcast name and logo, even though he designed the latter A whole lot more! Links Kneadle Christopher DeCaro on Twitter Get in touch! Come chat with us in our Slack team! Over 5,000 designers and develope...

25: Year End Couch Crunch
This episode is basically all the best ideas Brett and Andrew have ever had. All in one. Also, cupcakes. How to not crawl across the finish line and use year end to catch up Why sitting on the couch might be the most productive thing you do this week. Andrew realizes the whole world doesn't revolve around budgets. Or him. Brett expresses feelings. It does NOT end in tears. Instead, useful information What causes the changes is what we need to understand. Keep moving AND get out of the way. Get in touch! C...

24: Bill Bonfires (feat. David Sparks)
We love David Sparks and he is a super awesome lawyer. SO MUCH good information here What lawyers are good for (hint, it isn't war!) The basics of legal issues LLCs versus Corporations Why lawsuits are like lighting money on fire And so much more! Thanks to our sponsor! Check out Pluot, incredibly simple, very slick online meeting software. Click here to try Pluot for free! And don't forget FREE hardware through the end of January 2017 - just use the coupon code "Orthogonal" at checkout! You can find Davi...


23: Privilege Pants
This week, the dynamic duo discuss the limits of tech and tools, and how our attitudes influence our effectiveness with them. Entitlement culture Criteria for evaluating tools How Brett decides between web apps and native apps Brett kindly explains to Andrew why Gmail doesn't crash as often as Outlook Brett's one-minute hack for finding out an app's flaws Andrew says things, too. Thanks to our sponsor! Check out Pluot, incredibly simple, very slick online meeting software. Click here to try Pluot for free...

22: I'll Buy That Compost Aerator (The Bonus Holiday Episode)
This week, your two Santas bring you some good old fashioned, business-flavored holiday cheer! Topics include: Shopping on Black Friday Business lessons from upsell-crazy online and offline retailers Why Andrew's password manager sucks Why discounting something makes it more attractive to buyers The psychological tricks companies use to sell And a whole lot more fun and games! Well, no games. Fun, though. Don't forget to get our free business tips every week, right in your inbox. Sign up at getorthogonal....

21: Serendipitous Collaboration
Co-working spaces - WHO NEEDS 'EM? Turns out a lot of people, for various reasons. We dive into the whys and how of what makes them work and why we need to stay off Brett's lawn. Don't forget to get our free business tips every week, right in your inbox. Sign up at getorthogonal.com Thanks to our sponsor! Check out Pluot, incredibly simple, very slick online meeting software. Click here to try Pluot for free! Get in touch! Come chat with us in our Slack team! Over 5,000 designers and developers have already...


20: Expect The Unexpected
Look, your boys aren't afraid to have the hard conversations. As recent election results came in, things began happening in financial markets. If you want a quick, dirty, and surprisingly approachable explanation of why there are swings in stock prices, for example, this is your horse. Don't forget to get our free business tips every week, right in your inbox. Sign up at getorthogonal.com Thanks to our sponsor! Check out Pluot, incredibly simple, very slick online meeting software. Click here to try Pluot f...

19: Big Boy Pants Stuff
This week, your boys dive into the boring-yet-necessary core components of a successful financial life The document that you absolutely need (and probably don't have) Why you should take care of the boring stuff (because it's important) The Personal Finance Trifecta The one newbie move Andrew's clients pull all the time, and how to avoid this costly mistake And a whole heck of a lot more Don't forget to get our free business tips every week, right in your inbox. Sign up at getorthogonal.com Get in touch! ...

18: Who Wants This Pencil?
This week your favorite freelancing team discuss value and lists and why maintaining your relationships is quite possibly the most valuable work you can do. Also, where pencils come from. High points include: We steal other people's jokes before getting back to work. How to segment your audience by giving them the wrong bucket and supercharge your profitability. How the modern standard of value might be a well-defined audience, not a well-defined product. Why hanging out on Slack is actually work. ...


17: Not My Bucket
This week,snookums and CFO discuss authenticity, tribes, and why Brett doesn't like being a leader. Even though he is. High points include: The problems with the inherent superiority built into the term "leader" Why someone clicking unsubscribe isn't an insult. How not being afraid to look stupid is the key to authenticity. And why providing value is the only true way to demonstrate competency. Bonus: Andrew attempts to get Brett onboard the Pumpkin Spice train. Another bonus: Andrew's show notes are the ...

16: Dog Crap Pancakes
This week, your boys in pajamas discuss how they grow their respective businesses. It's a little longer than normal, but it's a good one. Nuggets include: Why Andrew doesn't ask for referrals (and gets them anyway) Brett explains the inner workings of email marketing (and describes, in detail, how he's going to grow a brand new business). Andrew's really glad to not be talking about S-Corps. Bonus: our biggest fan makes an in-person cameo appearance. Another bonus: Brett retakes control of the show notes ...

15: Don't Assume My Spreadsheet
This week, freelancers Snookums & Andrew review the ultimate checklist for an awesomely professional freelance business. (We are not making this up as we go along) We chat about: Entities (The S-Corp Flag) Books & budgets Payroll & W-2s Tax-themed knuckle tattoos How to avoid the guys in suits Bonus: Andrew literally cries. Other Bonus: Did you know people still use manual ledgers? Get a free transcript of today's show by visiting getorthogonal.com/podcast Get in touch! Come chat with us in our Slack team...


14: Nut 20
This week, your small business homeboys go deep on how to grow your business by what Andrew calls "niche-ing down." This technique will allow you to Increase your value relative to the competition Borrow from your current success so you can invest it back into your business Pull ahead of the pack by going deeper instead of wider in your offerings Take calculated risks that may work out to big increases in profit without working 60 hours per week like an animal And a whole gaggle more! Bonus: Andrew challe...

13: Humble Pie: Take & Bake
This week, your boys are back with another hard-hitting chat about launching a new product or business. Getting past the initial overwhelm of figuring out which of the million tasks need your attention is terribly important. Today, we'll show you how to do that. In this episode, you'll learn: The benefits of starting with a "minimum viable product" (and what that means) Your biggest enemy in getting your business off the ground Andrew's "minimum risk of loss" metric How Brett and Andrew built and launched ...

12: Smart Past, Dumb Now
This week, the dynamic duo talk about time, work, and budgeting for both. How Andrew budgets his time to accomplish everything he needs to do (which is a ton) Opportunity cost; don't be afraid to say no when the cost is too high Why you need to be ruthless with one person: yourself Your two different modes: planning and working Bonus: Andrew's excellent tip for handling overwhelm. Second bonus: Andrew makes up a Mark Twain quote. Don't forget to get our free business tips twice per week, right in your inb...


11: Freestyler Business Person
The most recent bee in Andrew's bonnet is The Three H's of Business Success... The Hacker, the Hustler, and the Hipster. (Brett is Andrew's hacker.) These three ingredients are the key to making delicious business pie. Stew? Anyway. Your boys will unpack why this is a sensible way to approach your business and how, in many cases, three heads are better than one. If you're looking for a succinct explanation of what "orthogonality" means, this is a great place to start. Learn more at getorthogonal.com. Get in...

10: Details, Schmetails
This week, your boys are talking about education. In particular, Andrew discusses books that Brett mostly hasn't read and why Brett really prefers learning from online products and courses. (Scroll down for the reading list from both of your favorite Internet dudes...) Sponsors: Thanks to our sponsor: FreshBooks — Get a free month here: http://spec.fm/freshbooks Get in touch! Come chat with us in our Slack team! Over 5,000 designers and developers have already joined our team, chatting about the latest to...

09: Cheese Plate Community Building
Today, your favorite gruesome twosome gets down and dirty with the idea of community. In particular, how freelancers and solo entrepreneurs can seek out the kind of community often found in 9-5 office jobs. Other nuggets: How Andrew splits his time between physical and digital networks and communities Brett makes fun of Andrew for talking like an old man (even though Brett is several years older) The one thing that used to be a requirement for community (...but not anymore) Why hyper-specialized communitie...


08: Tax Return Slot Machines
This week, your humble hosts dive into the sexiest of topics: taxes. In this action-packed episode, we discuss: The three types of tax deductions you can take as a freelancer (and how they work) More about Brett's Inverted Traffic Cone business money flow concept The best way to prepare yourself for tax season all year long Why the amount of tax you'll pay is not random and how you can actually know it beforehand. The hilarious tax return joke Andrew has yet to play on anybody For a very deep dive on tax ...

07: Braving the World of Strangers
The dynamic duo are back for another fun-filled chat. This week, it's all about finding new clients and customers for your freelance or independent business. Topics include: Why (and when) automation can be bad How Andrew grew his service business quickly The one place you're most likely to find new clients and customers The best thing you can do before you start your business to help ensure success (and how Brett did this for years before he launched). How to approach total strangers and, hopefully, turn ...

06: Funnel or Inverted Traffic Cone?
The boys are back for another fun-filled visit. This time around, we're talking about what it takes to leave your 9–5 job—Andrew calls them "jobby jobs"—and pursue a career as a freelancer or independent business owner. Specifically, we're discussing money. Specifics include: The three ways your company pays you that aren't your salary Why getting health insurance as a freelancer isn't nearly the massive obstacle most assume it is A handy formula for figuring out how much you need to bring in as a freelanc...


05: Habit Problems
In this very special episode, the dynamic duo continue the discussion of automation in very small business, including: How "partial automation" can help businesses that require a lot of one-on-one interaction The value of defined processes — planning a system beforehand so you can be dumb and just follow the instructions An overview of how Brett uses an elaborate email system to promote and sell his products Is outsourcing a form of automation? How to decide what should be automated (and what should not) ...

04: Automated Sniff Test
This week, the boys of summer tackle some important business questions: How valuable is automation in very small business? How do we humanize the parts of our businesses we automate? Why does Brett email his list so much? Can one be a cat lady and a chihuahua enthusiast? Huge takeaway from this episode: The super obvious 3-step formula for creating a profitable business (and that most Silicon Valley companies ignore) The genius of hyper-specialization in starting your business They also discuss specific...

03: Define Freelancer ...
This week, the boys unpack what it means to be a freelancer independent lifestyle business owner entrepreneur... thing; the good, the bad, and the ugly. In addition to the day-to-day experience, they also dig into some of the psychological challenges involved in independent work. And Brett tries some of Andrew's favorite coffee. Come chat with us in our Slack team! Over 5,000 designers and developers have already joined our team, chatting about the latest tools and news in the design world. To join our team...


02: Website Office Lobby
Today's episode is all about workspaces. Specifically... What does a workspace say about company culture? Does physical space create legitimacy?  How does your digital presence replicate the physical space? What affect does physical space have on your work? Also, Brett and Andrew are too clever for their own good. Come chat with us in our Slack team! Over 5,000 designers and developers have already joined our team, chatting about the latest tools and news in the design world. To join our team visit our Sl...

01: Pin Needle Freelance
We talk about the difficulty of defining our jobs and Andrew attempts to explain why we are becoming so much more specialized with economics. We discuss how this drives the move towards Freelance work and the trials and tribulations that come from that. Does not having a job make you more wealthy? Come chat with us in our Slack team! Over 5,000 designers and developers have already joined our team, chatting about the latest tools and news in the design world. To join our team visit our Slack invite page and...

00: Pamphlet Pros
Test, test. This is the intro. We'll talk a little bit about us, what we do, and why we started this podcast in the first place. If you have any comments for us or want to ask questions check us out at the Spec Network Slack: spec.fm/slack in the #orthogonal channel....