In Episode 554, Rob Walling chats with Sherry Walling about grief as a part of entrepreneurship and how to get better at handling grief as an entrepreneur. They also discuss burnout and properly evaluating if it's the right time to sell a company.



The topics we cover



[02:18] Grief is part of entrepreneurship



[05:12] Getting better at handling grief and loss



[06:07] Grief and selling a company



[09:01] The importance of symbols



[12:04] Evaluating reasons to sell a company



[16:37] The three components of burnout



[20:21] Changing your work schedule for summer



Links from the show




The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting it Run You



18 Summers



ZenFounder



Sherry Walling



Sherry Walling (@zenfounder) | 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!



Subscribe & Review: iTunes | Spotify | Stitcher

Episode 554 | Thinking Through Your Exit + Grief and Entrepreneurship with Dr. Sherry Walling

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 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 706.5 | Rethinking My Most Common Advice

MicroConf US in Atlanta is here in just a couple weeks, and this is your last call to buy tickets. We've sold more than 90% of the tickets, and we will sell this event out as we have for many years. The event is April 21st through the 23rd in Atlanta, Georgia at the amazing Starling Atlanta. 



There are going to be 200-ish of your closest bootstrapped and mostly bootstrapped founder friends who are showing up to hear talks from folks like Rand Fishkin of SparkToro, Asia Orangio of DemandMaven. I'm giving a talk as well, and Dr. Sherry Walling will be talking about staying motivated as an entrepreneur.

We have a special guest MC, Lianna Patch, and we'll have a very special guest who has never appeared on the MicroConf stage before- Ben Chestnut, the co-founder of MailChimp.



Get all the details and secure your ticket before they run out at microconf.com/americas.

Episode 554 | Thinking Through Your Exit + Grief and Entrepreneurship with Dr. Sherry Walling

Download our free app to listen on your phone