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.

• (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

• MicroConf Connect Applications open until January 15th
• TinySeed
• Invest with TinySeed
• Einar Vollset (@einarvollset) | X
• Episode 744 | Bluesky, TinySeed is Raising, YC Backs Competitors, and More Hot Take Tuesday Topics
• Discretion Capital
• How To Invest In Startups by Sam Altman

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

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.

• (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”

• SaaS Institute
• TinySeed
• Jane Portman (@uibreakfast) | X
• Jane Portman (@uibreakfast.com) | Bluesky
• Userlist
• Episode 471 | Fighting to Gain Traction in a Crowded Space with Jane Portman of Userlist
• Episode 742 | Normalizing Hard Things, Facing Your Biggest Threat, and Making it Fast (A Rob Solo Adventure)
• Crossing the Chasm by Geoffrey A. Moore
• Userlist Closes a Pre-Seed Round with 21 Angel Investors
• SaaS Email Marketing Strategy: Everything You Need to Know
• 20+ “Invite Your Team” Email Examples
• Atomic Emails: Our Proven Method for Writing Email Campaigns

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

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.

• (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

• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• Episode 697 | 7 Predictions for SaaS Bootstrappers in 2024
• Episode 725 | SEO in the Age of AI, Freemium, When Brand Becomes Important, and More Advanced Listener Questions (with Ruben Gamez)
• LINKLO
• TinySeed
• Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)

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

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.

• (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

• The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea”
• MicroConf YouTube Channel
• Episode 706 | 2/20/200 Validation, Prior Art, and Designing by Committee (A Rob Solo Adventure)
• TinySeed
• Vertical SaaS vs Horizontal SaaS - Which is More Profitable?
• Episode 735 | The 8 Levels of SaaS Platform Risk (A Rob Solo Adventure)
• The SaaS Playbook
• Episode 728 | Bootstrapping Gymdesk to a More Than $32.5M Exit
• Episode 706.5 | Rethinking My Most Common Advice
• Episode 729 | 9 Things I’ve Learned Investing in 170+ SaaS Companies
• Episode 709 | The 7 Greatest Investments of My Life
• Episode 694 | 2023 In Review: Amazing Growth & Fighting Burnout
• How Ben Chestnut Bootstrapped Mailchimp to a $12 Billion Exit
• MicroConf New Orleans 2025
• Start Small, Stay Small by Rob Walling
• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• TinySeed Tales

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.

• (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

• The SaaS Launchpad – Start Free with “The DNA of a Great SaaS Idea”
• Invest in TinySeed
• Rob Walling (@robwalling.com) | Bluesky
• TinySeed (@tinyseed.com) | Bluesky
• Tracy Osborn (tracymakes) (@tracyosborn.com) | Bluesky
• Einar Vollset (@einarvollset) | X
• Y Combinator often backs startups that duplicate other YC companies, data shows
• Procrastination and the Fear of Not Being 'Good Enough' by Swapnil Chauhan
• Startup Founders, Do THIS to Beat Imposter Syndrome
• Australia proposes 'world-leading' ban on social media for children under 16

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

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

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.

• (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

• 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 quest...

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!

• (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

• Exit Strategy: The Entrepreneur's Guide to Selling Your Business Without Regret
• MicroConf Masterminds Applications Close on December 4th
• Rob Walling (@robwalling) | X
• Dr. Sherry Walling (@sherrywalling) | X
• The Comic Lab Podcast
• The SaaS Playbook
• The Stair Step Method of Bootstrapping
• This Took 11 Years to Be An "Overnight Success" - SaaS Exit Strategy

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

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.

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.

• (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

• Mastermind Applications are open until December 4th
• Wes Bush (@wes_bush) | X
• ProductLed (@productled) | X
• ProductLed
• Product-Led Growth: How to Build a Product That Sells Itself by Wes Bush
• The Product-Led Playbook: How to Unlock Self-Serve Revenue and Dominate Your Market (With a Tiny Team) by Wes Bush
• Free Audiobook of The Product-Led Playbook
• Product-Led Onboarding by Ramli John
• TinySeed
• SparkToro
• SavvyCal

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!