Episode 836 | The 5 A.I. Moats Acquirers Value Most
Is your SaaS actually protected from AI disruption, or are acquirers walking away without even looking?
In this episode, Rob Walling talks with Einar Vollset of Discretion Capital for a front-lines SaaS M&A market report, covering how the acquisition climate has shifted since 2021, why some PE firms now require at least one AI moat before they'll even look at a deal, and a breakdown of all five moats: hardware-software coupling, two-sided network effects, communication graph embeds, proprietary data with closed feedback loops, and operational switching costs.
Topics we cover:
(2:05) – State of SaaS M&A from 2020 to today
(5:49) – Why 2021 was the best time to sell
(7:38) – How the 2022 downturn raised the acquisition bar
(8:59) – The SaaS apocalypse narrative and AI FUD
(12:26) – Why bootstrappers should care about exit markets
(15:52) – AI moat #1: Hardware-software coupling
(17:38) – AI moat #2: Marketplace scale and two-sided network effects
(20:05) – AI moat #3: Communication graph and relationship embed
(21:27) – AI moat #4: Proprietary data with closed feedback loops
(23:20) – AI moat #5: Operational embed and switching costs
(27:28) – Some PE firms now require at least one moat
(29:23) – AI-native SaaS faces even higher hurdles
Links from the show:
MicroConf Connect Next Live Session: Jim Zarkadas on User-Friendly Onboarding (June 17)
TinySeed
MicroConf YouTube
The SaaS Playbook
Discretion Capital M&A Guide
Fiscal.ai
DealForma
BuiltWith
ZyraTalk
EverCommerce
Einar Vollset (@einarvollset) | 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!
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Episode 827 | The Founder's Guide to Selling Your SaaS for What It's Actually Worth
What would it mean for you to leave 60 or 70% of your company's value on the table when you sell?
In this episode, Rob sits down with Einar Vollset, co-founder of TinySeed and founder of Discretion Capital, to talk about his new book, The Definitive Guide to M&A for B2B SaaS between $2 and $20 million ARR. They dig into why private equity now dominates the buyer landscape, why growth and churn are the top two valuation drivers, and how the myth that "startups are bought, not sold" could cost you millions.
Einar also explains the danger of running your business past its peak growth rate before selling, why ARR multiples matter more than profit, and how the right M&A advisor can add 30 to 300% to an initial offer.
Episode Sponsors:
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Topics we cover:
(3:34) – Why Einar wrote an M&A guide for SaaS founders
(5:26) – How founders leave value on the table when selling
(8:22) – How private equity moved down market
(11:24) – Choosing the right broker or banker
(12:55) – Platform acquisitions vs. tuck-ins explained
(19:24) – Why "startups are bought, not sold" is wrong
(25:48) – Growth and churn as top valuation drivers
(30:02) – Why ARR multiples matter more than profit
(34:34) – The danger of running past peak growth
Links from the show:
The Definitive Guide to M&A for B2B SaaS between $2–20M ARR
Discretion Capital
MicroConf US (Portland) - April 12-14, 2026
MicroConf Mastermind Matching
MicroConf Mastermind Playbook
TinySeed
Exit Strategy by Rob and Sherry Walling
The SaaS Playbook
ScrapingBee
Built to Sell by John Warrillow
Einar Vollset @einarvollset | X
If you have questions about starting or scaling a software business that you'd like for us to cover, pleasesubmit your question for an upcoming episode. We'd love to hear from you!
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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:
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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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:
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!
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Episode 727 | Gymdesk Sells for More than $32.5 million, Hiring Gets Easier, and More Hot Take Tuesday Topics
In episode 727, Rob Walling is joined by Tracy Osborn and Einar Vollset to give their hot takes on some recent news. First they celebrate Gymdesk’s recent funding and evaluate what that means for TinySeed companies. Then, they weigh in on bootstrapper hiring, grappling with new challenges as MRR grows, and how to really move the needle in your business.
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Topics we cover:
2:19 – Gymdesk Announces a $32.5 Million Strategic Growth Investment
9:06 – Is it getting easier for bootstrappers to hire?
12:22 – Facing different challenges as MRR grows
19:37 – Identifying what really moves the needle
23:56 – Listen to those who have built businesses before you
Links from the Show:
Subscribe to the Startups For the Rest of Us Email List
TinySeed
The SaaS Playbook
Discretion Capital
Tracy Osborn (@tracymakes) | X
Einar Vollset (@einarvollset) | X
TinySeed (@tinyseedfund) | X
Gymdesk Announces a $32.5 Million Strategic Growth Investment from Five Elms Capital
Eran Galperin (@erangalperin) | X
Episode 697 | 7 Predictions for SaaS Bootstrappers in 2024
State of Independent SaaS Report
The Elephant in the room: The myth of exponential hypergrowth
Traction by Gabriel Weinberg and Justin Mares
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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Episode 558 | Thinking Through Funding as a Bootstrapper
In Episode 558, Rob Walling chats with Einar Vollset about bootstrapping versus funding and the many options that exist in between. No longer is it a decision between a bootstrapped or venture path. With their unique perspectives, Rob and Einar talk about all of the funding options that exist. They also share some things to consider when deciding whether or not to take on funding and, if you do, how much you should plan on raising.
The topics we cover
[04:24] When funding makes sense for bootstrappers
[11:54] Raising pre-revenue vs raising with revenue
[15:29] Risks of raising as a platform (e.g. Shopify) business
[20:40] Funding options available to bootstrappers
[27:57] Convertible notes & SAFE's
[29:16] How much should a bootstrapper raise?
Links from the show
Episode 496 | "The Press Covers Exceptions, Don't Compare Yourself to Slack or Zoom"
Episode 411 | Bootstrapping vs. Funding: 19 Questions To Ask
Einar Vollset (@einarvollset) | 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!
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Episode 540 | Bootstrapper News. Twitter Spaces, Indie.vc Closing, Shopify, and More
In this episode, Rob talks with Tracy Osborn and Einar Vollset, about the recent news that's come out in the bootstrapper community. They talk about the Indie.vc shutdown, the new features coming out on Twitter, LinkedIn’s new gig marketplace, and more.
The topics we cover
[03:18] Twitter Spaces
[10:05] The Network Effect and Twitter Verification
[14:32] The Indie.vc shutdown
[24:20] Shopify removing the option to work directly with Stripe
[32:34] The new ‘Super Follow’ feature in Twitter
[35:43] Comparing Google Cloud and AWS onboarding
[40:04] The new LinkedIn Gig Marketplace
Links from the show
TinySeed
Tinyseed Thesis
Remail
Voxer
Shopify says remove Stripe billing or get booted from their app store
Substack
Indie.vc
Google Cloud vs AWS onboarding
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
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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Episode 538 | When to Sunset a Product, Enterprise Security Assessments, Lifetime Deals, and More Listener Questions
In this episode, Rob Walling is joined by Einar Vollset as they answer listener questions ranging from when to sunset a product, filling out enterprise security assessments, acquiring a company where the previous owner had sold lifetime deals and not disclosed it, and more.
The topics we cover
[03:20] Deciding when to sunset a feature or product
[08:27] Splitting a business to focus on two separate audiences
[17:21] How to take advantage of being a consumer of your own product.
[21:35] Acquiring a SaaS where the previous founder sold lifetime plans
[28:20] Enterprise security assessments
[35:22] Building a product to solve a problem as a full-time employee
Links from the show
TinySeed Tales S2E1 | Introducing Gather
Episode 515 | Finding a Co-Founder, Getting Better at Sales, and More Listener Questions
Episode 9: Raising Entrepreneurial Kids - ZenFounder
SOC 2
Episode 463 | Troubleshooting Enterprise Sales (A Founder Hotseat with David Heller)
The TinySeed Investment Thesis — TinySeed: The Startup Accelerator for Bootstrappers
Einar Vollset (@einarvollset) | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
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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Episode 521 | A Roundtable Discussion about a Potential Recession, Working from Home, Google Anti-trust, and More
Episode 521 is a roundtable episode where Rob brings on a couple of guests to talk through topics today that relate to bootstrapped and mostly bootstrapped startup founders.
Today, we have Tracy Osborn and Einar Vollset joining us, as we talk through a potential impending recession, the Google anti-trust suit, Dropbox moving to permanent work from home, as well as a handful of other topics.
The topics we cover
[04:03] What do the revenue trends look like in 6-7 months from now?
[13:36] Google anti-trust suit
[19:23] Dropbox remote offices
[27:29] SPACs and why it's so hard to go public in the US
[39:35] A warning about Glassdoor
Links from the show
The 99 Investor Problem
U.S. Accuses Google of Illegally Protecting Monopoly
Dropbox will let all employees work from home permanently as it turns its offices into WeWork-like 'collaborative spaces'
The TinySeed Investment Thesis
A Warning About Glassdoor
Tracy Osborn | Twitter
Einar Vollset | Twitter
If you enjoyed this episode, let us know by clicking the link and sharing what you learned.
Click here to share your number one takeaway from the episode.
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