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!

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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!

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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