In Episode 588, Rob Walling chats with Courtland Allen about a wide range of bootstrapper and indie hacker topics including the struggles with motivation/depression, bootstrapping today, fighting the urge to quit, and frameworks for getting your first dollar.



The topics we cover



[3:43] Hiring a podcast producer



[6:21] Letting go in business



[7:09] Invite-only experiment on Indie Hackers



[16:03] Thinking about the future



[20:47] Financial freedom and starting a business



[25:05] Depression as a founder and rediscovering purpose



[37:10] Fighting the urge to quit



[41:10] Getting your first dollar



[52:35] The bootstrapper scene in 2010 and the relevance of bootstrapping



Links from the show




Rob Walling on Twitter



The Time Paradox: The New Psychology of Time That Will Change Your Life



Courtland Allen (@csallen) | Twitter




If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you!



Also, if you haven't seen, applications are open for TinySeed's Spring 2022 programs. TinySeed is a year-long remote accelerator program is designed to help founders with a revenue-generating SaaS optimize product-market fit and grow faster. Read about the program and how to apply here.



Subscribe & Review: iTunes | Spotify | Stitcher

Episode 588 | In Which Courtland Allen and I Cover a Lot of Startups Topics

The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.

Business

Investing

Careers

Management & Marketing

Business News

Shopping

Marketing

Management

Entrepreneurship

In episode 710, join Rob Walling for another solo adventure where he answers listener questions. He answers whether you need a burning passion to be successful in entrepreneurship, and how that relates to developing a product alongside a day job. Rob also discusses competing against VC-backed companies, learning to code in the age of AI, and how much risk lies in IP theft when building your SaaS.



Episode Sponsor:





Is your outsourced development team dropping the ball?



Maybe you’ve worked with a team that just couldn't grasp your vision and needed constant oversight because they weren’t thinking strategically. Or maybe you ended up wasting hours micromanaging, often needing to jump on late-night calls across massive time zone differences to get alignment. And in the end, they delivered a sluggish app with a frustrating UI that didn’t come close to the solution you had envisioned. If any of that sounds familiar, you need to reach out to our sponsor - DevSquad.



DevSquad provides an entire development team packed with top talent from Latin America. 



Your elite squad will include between 2 to 6 Full Stack Developers, a technical product manager, plus experts in product strategy, UI/UX design, DevOps, and QA - all working together to make your SaaS Product a success.



You can ramp up an entire product team fast, in your timezone, and at rates 75% cheaper than a comparable US-based team. And with DevSquad, you pay month to month with no long-term contracts. 



Get the committed, responsive development team that your business deserves.  



Visit DevSquad.com/startups and get 10% off the first three months of your engagement.



Topics we cover: 




3:00 – Reacting to needing a burning desire for entrepreneurship



5:20 – Maintaining a day job to enable space for entrepreneurial pursuits



8:52 – Balancing build speed vs. scalability with your tech stack



10:30 – The April Fools Episode



12:55 – Competing against VC-backed companies in a “hot” space



18:34 – Is learning to code dead?



27:33 – Risk in SaaS of IP theft




Links from the Show: 




MicroConf Connect



Episode 704 | Landing Pages, Buying a SaaS, the Right Tech Stack, and More Listener Questions



Episode 706.5 | Rethinking My Most Common Advice



The SaaS Playbook by Rob Walling



Start Small Stay Small by Rob Walling



TinySeed



Episode 688 | Growing Boot.dev From $6k to $110k in Monthly Revenue in 15 Months



Ask a Question on SFTROU

Episode 710 | Is Coding Dead?, The "Right" Tech Stack, Funded Competition, and More Listener Questions

In episode 709, join Rob Walling for a solo adventure as he shares his story of growing his personal wealth over the past few decades. Selling companies was the major driver of wealth, but he also explores the role of cryptocurrency, running profitable companies, and angel investing. Rob emphasizes the power of entrepreneurship in achieving financial freedom, while acknowledging there are ways to do so while keeping risk relatively low.



Episode Sponsor:





We have been partnering with Lemon.io for several years, and they’ve proven to be a great choice when it comes to hiring for a highly skilled developer to work on your project.



Here are five reasons why you should consider working with Lemon.io.




The time from your request to getting a candidate is just 48 hours.



Developers have previously worked with tech giants such as Apple, Google, Netflix, Airbnb, Intel, and LEGO. 



They only provide senior devs, with an average of 7 years' experience.



Their talent pool covers more than 300 dev languages & frameworks.



Your hire comes with a zero-risk, replacement guarantee.




Customers of Lemon.io typically stick around for at least a year, proving they know how to gain your trust by delivering consistent results.



Quit wasting time searching for a solid developer at a great price. Get in touch with Lemon.io.



As a bonus for our podcast listeners, you’ll get a 15% discount on your first four weeks of working with a developer at lemon.io/startups. That’s lemon.io/startups



Topics we cover: 




2:50 – A lesson on how to build wealth



4:31 – Entrepreneurship was our biggest tool



6:37 – Building, acquiring, then selling companies



10:45 – Building slowly while staying risk-averse



13:27 – Investing in riskier assets like cryptocurrency



19:39 – Running profitable companies



20:56 – Angel investing, and WP Engine



23:44 – Traditional, salaried employment



24:53 – Typical investments: stocks, bonds, REITs



27:36 – Real estate investing




Links from the Show: 




MicroConf Connect



Christopher Gimmer (@cgimmer) | X



Christopher’s tweet



Sherry Walling (@sherrywalling) | X



The Stair Step Method of Bootstrapping



Start Small Stay Small by Rob Walling



This Took 11 Years to Be An "Overnight Success" - SaaS Exit Strategy



Zen Founder



The SaaS Playbook by Rob Walling



WP Engine



TinySeed



Barbell Strategy Explained for Stock and Bond Investors




If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode.

Episode 709 | The 7 Greatest Investments of My Life

In episode 708, Rob Walling and Derrick Reimer tackle listener questions about building development skills vs. business skills and strategies for entering competitive markets. They also chat about building on top of AI services, addressing the risks of platform dependency and the importance of managing infrastructure costs. 



Episode Sponsor:





Is your outsourced development team dropping the ball?



Maybe you’ve worked with a team that just couldn't grasp your vision and needed constant oversight because they weren’t thinking strategically. Or maybe you ended up wasting hours micromanaging, often needing to jump on late-night calls across massive time zone differences to get alignment. And in the end, they delivered a sluggish app with a frustrating UI that didn’t come close to the solution you had envisioned. If any of that sounds familiar, you need to reach out to our sponsor - DevSquad.



DevSquad provides an entire development team packed with top talent from Latin America. 



Your elite squad will include between 2 to 6 Full Stack Developers, a technical product manager, plus experts in product strategy, UI/UX design, DevOps, and QA - all working together to make your SaaS Product a success.



You can ramp up an entire product team fast, in your timezone, and at rates 75% cheaper than a comparable US-based team. And with DevSquad, you pay month to month with no long-term contracts. 



Get the committed, responsive development team that your business deserves.  



Visit DevSquad.com/startups and get 10% off the first three months of your engagement.



Topics we cover: 




02:38 - Should you build technical skills or business skills?



11:41- Entering a competitive market



21:14 - Building a valuable analytics dashboard tool



29:29 - When should a solo founder hire for marketing roles?



36:29 - The rare skillset of a full-stack marketer 



38:18 - Implications of building on openAI and scaling infrastructure costs




Links from the Show: 




Register for MicroConf US in Atlanta, April 2024



Rob Walling | X



Derrick Reimer | X



Derrick Reimer



SavvyCal



Start Small Stay Small by Rob Walling



The SaaS Playbook by Rob Walling



Devin AI




If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!
Subscribe & Review: iTunes | Spotify

Episode 708 | Outsourcing Marketing, Competitive Markets, and More Listener Questions (with Derrick Reimer)

In episode 707, Rob Walling, alongside guests Tracy Osborn and Einar Vollset, give their hot takes on some recent news in the world of SaaS. They discuss Once.com’s launch, liquidation preference nuances in startup buyouts, with moving from open source to full time income and more. 



Episode Sponsor:





Find your perfect developer or a team at Lemon.io/startups



The competition for incredible engineers and developers has never been more fierce. Lemon.io helps you cut through the noise and find great talent through its network of engineers in Europe and Latin America.



They take care of the vetting, interviewing, and testing of candidates to make sure that you are working with someone who can hit the ground running.



When it comes to hiring, the time it takes to write your job description, list the position, review resumes, schedule interviews, and make an offer can take weeks, if not months. With Lemon.io, you can cut down on a lot of that time by tapping into their wide network of developers who can get started in as early as a week.



And for subscribers of Startups For the Rest of Us, you can get 15% off your first 4 week contract with a developer by visiting lemon.io/startups



Topics we cover: 




2:18 - Once.com and the Implications of One-Time Software Sales



10:39 - Liquidation Preferences in Startup Acquisitions



21:59 - Turning an open source project into a business



24:32 - Book recommendations



30:30 - Is building a startup actually hard?



32:46 - Startups vs. lifestyle businesses




Links from the Show: 




Register for MicroConf US in Atlanta, April 2024



Once.com



Campfire



Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld



Never Split the Difference by Chris Voss



The Anomaly by Herv Le Tellier



The Art of Learning by Josh Waitzkin



The Beginning of Infinity by David Deutsch



TinySeed



Einar Vollset (@EinarVollset) | X



Tracy Osborn (@itsTracyMakes) | TikTok




If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!




Subscribe & Review: iTunes | Spotify | Google

Episode 707 | Once.com, Open Source to FT Income, and More (Hot Take Tuesday)

In episode 706.5, join Rob Walling as he reconsiders some of his most common advice. He explores why lowering prices might make sense and discusses the benefits of a B2C business model. Rob also walks back his prior advice on bootstrapping two-sided marketplaces and launching multiple products to see what sticks. 



Topics we cover: 




1:04 – What would happen if you lowered prices?



3:56 – Benefits of a B2C approach



7:05 – Two-sided marketplaces allow to reach two audiences



8:47 – Launch a bunch of products to see what sticks



10:52 – This episode was released April 1, 2024




Links from the Show: 




The SaaS Playbook



Rob Walling (@robwalling) | X




If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!



Subscribe & Review: iTunes | Spotify | Google

Episode 588 | In Which Courtland Allen and I Cover a Lot of Startups Topics

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