Startups For the Rest of Us

Startups For the Rest of Us

Rob Walling

The most popular podcast for bootstrapped and mostly bootstrapped startup founders

26 minutes 8 seconds

Episode 749 | TinySeed Tales s4e1: Introducing Hammerstone.dev
Welcome to Season 4 of TinySeed Tales, where we follow the founders of one SaaS startup throughout a few years as they share their struggles, victories, and failures.

In the first episode of Season 4, Rob introduces us to Colleen Schnettler, the cofounder of Hammerstone. Colleen is a self-taught Rails developer, and this season will follow how Hammerstone eventually becomes Hello Query – an AI-powered chatbot that runs custom reporting on your data. Colleen is one of 27 startup founders from TinySeed’s Fall 2022 accelerator batch.

Topics we cover:
- (2:16) – TinySeed Tales Season 4 with Colleen Schnettler
- (3:57) – Custom reporting in Laravel and Rails
- (7:05) – Becoming an “atypical founder”
- (14:11) – Entrepreneurship as a military spouse
- (16:17) – Motivations for joining TinySeed
- (19:15) – A recent low point, and high point in the business
- (25:00) – Big plans and risky moves ahead
Links from the Show:
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
16 January 2025, 10:00 am
38 minutes 43 seconds

Episode 748 | The Ins and Outs of Startup Investing
In episode 748, Rob Walling sits down with Einar Vollset, co-founder of TinySeed, to discuss the ins and outs of startup investing. They explore the differences between VC and angel investing, the importance of deal flow, and the challenges of valuation. Rob and Einar also highlight how TinySeed’s approach differs from traditional VC, including their focus on capital efficiency and why it’s been working for ambitious B2B SaaS companies.

Topics we cover:
- (2:37) – The stigma of bootstrapper funding is waning
- (6:44) – What success looks like in venture funding
- (10:45) – Breaking down the math and deal flow
- (17:54) – How valuations work
- (26:21) – Keeping optionality
- (29:58) – Evaluating markups
- (35:18) – Raising TinySeed’s next fund
Links from the Show:
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
14 January 2025, 10:00 am
35 minutes 54 seconds

Episode 747 | Evolving SaaS Customer Success Over 7 Years (with Jane Portman)
In episode 747, Rob Walling interviews Jane Portman, co-founder of Userlist, to discuss the evolution of their SaaS customer success strategy. Jane shares the four stages of Userlist’s customer success journey, from the early days of trial and error to implementing done-for-you services. They also discuss the challenges of customer onboarding for complex products.

Topics we cover:
- (2:20) – How customer success works at Userlist
- (5:27) – Dealing with upfront onboarding friction
- (9:51) – Stage 1, “young and naive”
- (12:16) – Stage 2, “hire someone”
- (19:06) – Stage 3, “done for you services”
- (25:47) – Leveraging the Userlist blog
- (29:26) – Stage 4, “developing your own frameworks”
Links from the Show:
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
7 January 2025, 10:00 am
22 minutes 25 seconds

Episode 746 | 9 Startup Predictions for 2025
In episode 746, Rob Walling looks ahead to 2025 with nine startup predictions, exploring trends in no-code tools, search, autonomous vehicles, AI, and an increase in platform risk for bootstrapped founders.

Topics we cover:
- (1:52) – Carrying forward predictions from 2024
- (3:09) – Search volume for Google organic SEO
- (6:34) – Ads in AI interfaces
- (7:50) – Google’s revenue drops, bootstrapper opportunities
- (10:07) – “AI” use in H1’s
- (14:01) – Self-driving taxis
- (19:28) – Platform risk intensifies
Links from the Show:
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
31 December 2024, 10:00 am
27 minutes 21 seconds

Episode 745 | Reflecting on 2024: Revisiting My Predictions, The Best Episodes, My Favorite Frameworks, and More (A Rob Solo Adventure)
In episode 745, Rob Walling goes solo to reflect on 2024. He revisits key concepts and frameworks introduced on the podcast, including the 2-20-200 Validation Framework, Orthogonal SaaS, and the eight levels of platform risk. Rob also looks back at his top five favorite episodes and reviews his predictions for the year—some of which came to pass, and others that didn’t.

Topics we cover:
- (2:05) – Looking back at concepts and frameworks from past 12 months
- (8:50) – Rob’s 5 favorite episodes
- (11:56) – Reflecting on 2024 accomplishments
- (19:47) – TinySeed Tales Returns in 2025
- (21:18) – Evaluating 2024 predictions
Links from the Show:
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
24 December 2024, 10:00 am
33 minutes 57 seconds

Episode 744 | Bluesky, TinySeed is Raising, YC Backs Competitors, and More Hot Take Tuesday Topics
In episode 744, Rob Walling is joined by Tracy Osborn and Einar Vollset to give their hot takes on some recent news. They cover the recent rise of Bluesky, kicking off a 4-figure bet between Tracy and Einar. Then they discuss TinySeed’s third fund, YC Combinator backing competitors, dealing with imposter syndrome, and finally government involvement in banning social media.

Topics we cover:
- (1:49) – Will Bluesky survive and thrive?
- (9:07) – The bet on Bluesky growth
- (13:46) – TinySeed is raising a third fund
- (17:25) – Y Combinator backs duplicates
- (22:18) – Dealing with Imposter Syndrome
- (27:46) – Australia's social media ban
Links from the Show:
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
17 December 2024, 10:00 am
36 minutes 42 seconds

Episode 743 | How to Sell Your Business Without Regret
In episode 743, Rob Walling and Dr. Sherry Walling read the first chapter of their new book, Exit Strategy: The Entrepreneur’s Guide to Selling Your Company Without Regret. They discuss the emotional and psychological challenges of selling a business, and why it’s often harder than founders expect. They offer insights on how to prepare for a sale, protect your mental health, and how to best navigate this major life change that few others understand.

Back the book on Kickstarter

Episode Sponsor:

Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io.

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.”

Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer.

To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups.

Topics we cover:
- (1:49) – Exit Strategy Introduction
- (6:56) – Exits are complicated
- (11:16) – One of the hardest things you’ll ever do
- (15:57) – Your business is your baby
- (18:35) – Entering the unknown
- (26:49) – Six factors that shape how you feel about an exit
- (31:03) – Making it real
Links from the Show:
- Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
- Back the book on Kickstarter
- MicroConf Connect Applications Close Today, December 10th
- Rob Walling (@robwalling) | X
- Dr. Sherry Walling (@sherrywalling) | X
- The SaaS Playbook
- Built to Sell by John Warrillow
- Touching Two Worlds by Dr. Sherry Walling
- The Entrepreneur’s Guide to Keeping Your Sh*t Together by Sherry Walling, PhD, Rob Walling
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
10 December 2024, 10:00 am
28 minutes 21 seconds

Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure)
In episode 742, Rob Walling goes solo to explore normalizing doing hard things and facing your biggest threats. He also discusses a framework for founders looking to scale without cutting corners – making things work, making them right, and then making them fast.

Exit Strategy Kickstarter ends on December 12!

Topics we cover:
- (2:39) – Normalizing doing hard things
- (6:54) – The “hard things” in your startup
- (10:27) – Walking into the storm
- (16:21) – ”Make it work, make it right, make it fast”
- (22:04) – Building your “Founder Gut”
- (25:42) – Think in years, not months
Links from the Show:
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
3 December 2024, 10:00 am
31 minutes 48 seconds

Episode 741 | What Actually is Product Led Growth? (with Wes Bush)
In episode 741, Rob Walling talks to Wes Bush, CEO and Founder of ProductLed, about the nuances and misconceptions of product-led growth. Wes debunks common myths and explains how companies can leverage their product to drive user acquisition, engagement, and growth. They dive into a real-world example and explore how founders can avoid the trap of thinking the product will “sell itself” while contrasting PLG and sales-led strategies.

Episode Sponsor:

Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io.

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.”

Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer.

To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups.

Topics we cover:
- (2:01) – Defining product-led growth
- (6:07) – Are users able to get value for free?
- (11:38) – Hybrid: both product-led and sales-led
- (14:52) – Determining the main outcome of your free model
- (19:23) – Misuse of the PLG terminology
- (22:00) – The benefits of PLG over sales-led growth
- (24:08) – Workshopping SavvyCal’s product-led strategy
Links from the Show:
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
26 November 2024, 10:00 am
29 minutes 49 seconds

Episode 740 | My New Book! The Entrepreneur's Guide to Selling Your Business Without Regret
In episode 740, Rob Walling speaks with Dr. Sherry Walling about their new book, "Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret." They explore the emotional, psychological, and practical aspects of selling a business, emphasizing the universal challenges entrepreneurs face. The book draws on both Rob and Sherry’s unique experiences that they’ve shared with countless founders throughout their careers.

Exit Strategy is now live on Kickstarter!

Topics we cover:
- 2:01 – Not just a book for those selling SaaS
- 8:13 – The Kickstarter for the book is live today
- 12:16 – Before, during, and after the exit
- 14:55 – Why exiting is so hard
- 20:39 – Life after the exit
- 25:10 – A few traps await founders shortly after exit
- 26:24 – What do you do with a big pile of money?
Links from the Show:
- MicroConf Remote Goes Live November 20th!
- Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
- Rob Walling (@robwalling) | X
- Dr. Sherry Walling (@sherrywalling) | X
- Zen Founder
- Zen Founder Podcast
- The SaaS Playbook
- The Art of Selling Your Business by John Warrillow
- Before the Exit by Dan Andrews
- Finish Big by Bo Burlingham
- MicroConf
- TinySeed
- Touching Two Worlds by Dr. Sherry Walling
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
19 November 2024, 10:00 am
29 minutes 38 seconds

Episode 739 | Selling SaaS to Customers Who Don't Know They Have a Problem
In episode 739, Rob Walling interviews Andy Kim, co-founder of Trotto, about his unique journey into SaaS. Andy shares how “go links” work, and why they are so valuable for internal, enterprise use despite their relative obscurity. They also explore the marketing hurdles and customer adoption challenges in a business like Trotto.

Episode Sponsor:

Hiring senior developers can really move the needle in your business, but if you bring on the wrong person, you can quickly burn through your runway. If you need help finding a vetted, senior, results-oriented developer, you should reach out to today’s sponsor, Lemon.io.

For years, they’ve been helping our audience find high quality, global talent at competitive rates, and they can help you too.

Longtime listener Chaz Yoon, hired a senior developer from Lemon.io and said his hire ”definitely knew his stuff, provided appropriate feedback and pushback, and had great communication, including very fluent English. He really exceeded my expectations.”

Chaz said he’d definitely use Lemon.io again when he’s looking for a senior level engineer.

To learn more and get a 15% discount on your first four weeks of working with a developer at lemon.io/startups.

Topics we cover:
- 3:13 – Go links, URL shorteners for enterprise
- 6:14 – History of the problem and core users
- 9:44 – Customer education and growth opportunities
- 15:37 – Finding the repeatable marketing funnel
- 21:07 – Buying into a co-founder role at Trotto
- 24:42 – What’s the hardest part of running Trotto?
Links from the Show:
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
12 November 2024, 10:00 am
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Startups For the Rest of Us

Rob Walling

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