Episode 838 | 6 Key Takeaways From a TinySeed Batch Kick-Off artwork

Episode 838 | 6 Key Takeaways From a TinySeed Batch Kick-Off

Startups For the Rest of Us

June 23, 2026

What do 15 brand-new TinySeed founders have in common?  In this solo episode, Rob Walling shares six key takeaways from the most recent TinySeed batch kickoff in New York City.
Speakers: Rob Walling, Keith Shields
**Rob Walling** (0:00)
For example, if you're 5X underpriced, what you could be charging, you will build a $250,000 business at best when it should be a $1.25 million business. And frankly, if you're that far underpriced, you're probably not going to have the money to market and sell it in the way that it needs to be to be a successful business. Underpricing, bad value metrics, pricing that's overly complicated, there's a bunch of different ways to do it wrong. And there's only a few ways to do it right.
It's another episode of Startups For the Rest of Us. I'm your host, Rob Walling, and in this episode, I talk about six things that I took away from our recent TinySeed batch kickoff. We did it just a couple of weeks ago in New York City, and in these small group settings, I always notice struggles that many founders are experiencing, and other things that I think would be helpful for you as a bootstrapped or mostly bootstrapped founder. But before I dive into those, I want to let you know about the SAS Institute. It is our premium coaching for seven and eight-figure SAS founders. We have B2B founders, we have B2C, and we are growing. So we've recently added two new coaches, Julian Marzouk and Ryan Angley. SAS Institute is for founders who want community, who want coaching one-on-one and in a mastermind setting, and want advice from mentors like myself. And if you go to tinyseed.com/mentors, you can see the stable of mentors that you can tap into as a SAS Institute founder. We also have a couple in-person events each year that are very small, like 10 to 15 people, I believe. And the founders in SAS Institute are executing at a very high level. It's an amazing group to be part of. So if you're a seven- or eight-figure founder and you've been looking for community, mentorship, advice, coaching, masterminding, you should head to sasinstitute.com.
And with that, I want to dive into six key takeaways that I pulled from our TinySeed kickoff. A couple weeks ago, as I sat in a beautiful conference room in an amazing hotel that producer Sonia picked for us in the Chelsea district of Manhattan, and Anar Volsed and myself and Alex Craig and producer Sonia hung out with about 15, I'm kind of guessing, but about 15 TinySeed founders. Brand new. It's about batch 19 or 20, probably. It brings our total number of companies funded to 217
And now myself up to 241 investments in SaaS companies. But we spent a pretty incredible two and a half days together. We had some dinners. We had some walks around Manhattan. We had some activities. You could call them team building, but it's just fun to meet the new founders and to build that camaraderie within that group, within the batch. We found that these kickoffs and these in-person events are so crucial to forming that cohesion that is going to have the batch really help one another. You know, because TinySeed is such an amazing network now of mentors, investors, founders, and having a kind of a smaller group that you can belong to, like your batch, and it's like your high school class or your college class, is super important. And when you enter the room the first night, it's kind of awkward and you don't know any of the founders around the table, and by the time we all leave two and a half days later, all of us feel like we know each other and like we've shared so much experience and like I know their business is so much better than the day we arrived. During the work sessions, which we have a solid one each day, we did some masterminding. We went around the room to all the founders and said, what tactic or strategy are you using with sales and marketing that is really working for you now? And I love it's one of my favorite parts of the event, because I hear things that you don't see out in the wild. You don't see people talking about on ex Twitter. I don't have them in my book. Like people are being super creative, and they're coming up with new and innovative ideas to find new leads to close new deals. And then we have our famous pricing reviews or pricing teardowns, where Craig Hewitt, Interval Set, and myself go through every founder's pricing with say with a fine tooth comb. I mean, we basically spend about 20 minutes, which doesn't sound like a lot. You can really dig in. I mean, we are pattern matching based on hundreds and hundreds. Like we've seen bad pricing from folks that we haven't funded. We've seen good pricing for folks we funded, but most of the pricing we see has some issues. About 80% of any batch has an issue with the pricing. Sometimes they need to raise it. It's not always, but sometimes they need to raise it. Sometimes their pricing is just too complicated, and they need to dramatically simplify it. And other times their value metric is off. They're not measuring the right thing. And through conversations with the founders in the room, everybody's in the room at once, and we just go around the room 20 minutes at a time. Really informative, and folks can start seeing our rules of thumb, the ways that we think about and evaluate pricing. And we dig into it this early, because if your pricing's off, like it's the biggest lever in SaaS, right? I say this all the time, and if your pricing's off, it can be very hard nigh impossible to build a great seven or eight figure business. So that was the general course of events over those few days, and now I want to dive in to my six takeaways. The first one is the importance of asking why. It's the importance of finding a root cause, and you don't even need to do the five whys. You may have heard of five whys. Oftentimes it's just one why.

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