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Oct 14, 2025 · 16m · startup-acquisition-stories

From Two Small Projects to Profitable Exits on Acquire.com

Tom Ulman · 11m spoken Andrew Gazdecki · 2m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of Startup Acquisition Stories, host Andrew Gazdecki interviews designer and entrepreneur Tom Ulman about revitalizing, monetizing, and successfully exiting two micro-SaaS projects on Acquire.com to fund his growth agency and long-term holding portfolio.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Andrew holds 20.4% of the talking time here. How this is scored →

Andrew as informed peer 2.9 Guest teaching 2.1 Guest disagreement 0.0 Andrew pushing back 0.1
05100:0010:000:24–4:13 · Andrew as informed peer 3/10 Meet Tom Ulman: Founder of Almost Human Digital Andrew prompts Tom on how he acquired waitlist.email and Text.run, and how he grew user engagement. Tom explains his strategy of eliminating free pricing tiers and learning from users, which Andrew validates enthusiastically.4:14–7:16 · Andrew as informed peer 4/10 Managing and Maintaining Text.run Andrew offers ideas on buying SaaS companies and suggests core growth levers like price increases. Tom agrees, laying out his top growth levers including organic directories and SEO optimization.7:17–9:43 · Andrew as informed peer 4/10 Pricing Strategies and Lifetime Deals Andrew brings up the trade-offs of lifetime deals, highlighting the risk of ongoing support costs versus upfront cash. Tom responds with practical ways to mitigate risks by limiting upgrade periods and tiers.9:44–11:47 · Andrew as informed peer 2/10 The Decision to Sell and Transition Andrew inquires about the decision to sell and the experience with buyers on Acquire.com. Tom explains his motivation to inject capital into his agency and describes how fast the sales closed.11:48–14:06 · Andrew as informed peer 5/10 Acquisition Learnings and Leveraging AI Tom talks about utilizing AI to assist in due diligence and account handovers. Andrew shares Acquire.com internal best practices for prompting LLMs to review LOIs and evaluate acquisition offers.14:07–16:12 · Andrew as informed peer 2/10 Advice for Prospective Startup Sellers Tom advises founders to use Acquire.com for seamless small transactions and describes his new agency focus. Andrew wraps up the interview on an amicable and supportive note.16:13–16:43 · Andrew as informed peer 0/10 Podcast Conclusion and Acquire.com Information Standard promotional outro monologue read by the voiceover with no dialogue or debate.0:24–4:13 · Guest teaching 3/10 Meet Tom Ulman: Founder of Almost Human Digital Andrew prompts Tom on how he acquired waitlist.email and Text.run, and how he grew user engagement. Tom explains his strategy of eliminating free pricing tiers and learning from users, which Andrew validates enthusiastically.4:14–7:16 · Guest teaching 2/10 Managing and Maintaining Text.run Andrew offers ideas on buying SaaS companies and suggests core growth levers like price increases. Tom agrees, laying out his top growth levers including organic directories and SEO optimization.7:17–9:43 · Guest teaching 3/10 Pricing Strategies and Lifetime Deals Andrew brings up the trade-offs of lifetime deals, highlighting the risk of ongoing support costs versus upfront cash. Tom responds with practical ways to mitigate risks by limiting upgrade periods and tiers.9:44–11:47 · Guest teaching 3/10 The Decision to Sell and Transition Andrew inquires about the decision to sell and the experience with buyers on Acquire.com. Tom explains his motivation to inject capital into his agency and describes how fast the sales closed.11:48–14:06 · Guest teaching 2/10 Acquisition Learnings and Leveraging AI Tom talks about utilizing AI to assist in due diligence and account handovers. Andrew shares Acquire.com internal best practices for prompting LLMs to review LOIs and evaluate acquisition offers.14:07–16:12 · Guest teaching 2/10 Advice for Prospective Startup Sellers Tom advises founders to use Acquire.com for seamless small transactions and describes his new agency focus. Andrew wraps up the interview on an amicable and supportive note.16:13–16:43 · Guest teaching 0/10 Podcast Conclusion and Acquire.com Information Standard promotional outro monologue read by the voiceover with no dialogue or debate.0:24–4:13 · Guest disagreement 0/10 Meet Tom Ulman: Founder of Almost Human Digital Andrew prompts Tom on how he acquired waitlist.email and Text.run, and how he grew user engagement. Tom explains his strategy of eliminating free pricing tiers and learning from users, which Andrew validates enthusiastically.4:14–7:16 · Guest disagreement 0/10 Managing and Maintaining Text.run Andrew offers ideas on buying SaaS companies and suggests core growth levers like price increases. Tom agrees, laying out his top growth levers including organic directories and SEO optimization.7:17–9:43 · Guest disagreement 0/10 Pricing Strategies and Lifetime Deals Andrew brings up the trade-offs of lifetime deals, highlighting the risk of ongoing support costs versus upfront cash. Tom responds with practical ways to mitigate risks by limiting upgrade periods and tiers.9:44–11:47 · Guest disagreement 0/10 The Decision to Sell and Transition Andrew inquires about the decision to sell and the experience with buyers on Acquire.com. Tom explains his motivation to inject capital into his agency and describes how fast the sales closed.11:48–14:06 · Guest disagreement 0/10 Acquisition Learnings and Leveraging AI Tom talks about utilizing AI to assist in due diligence and account handovers. Andrew shares Acquire.com internal best practices for prompting LLMs to review LOIs and evaluate acquisition offers.14:07–16:12 · Guest disagreement 0/10 Advice for Prospective Startup Sellers Tom advises founders to use Acquire.com for seamless small transactions and describes his new agency focus. Andrew wraps up the interview on an amicable and supportive note.16:13–16:43 · Guest disagreement 0/10 Podcast Conclusion and Acquire.com Information Standard promotional outro monologue read by the voiceover with no dialogue or debate.0:24–4:13 · Andrew pushing back 0/10 Meet Tom Ulman: Founder of Almost Human Digital Andrew prompts Tom on how he acquired waitlist.email and Text.run, and how he grew user engagement. Tom explains his strategy of eliminating free pricing tiers and learning from users, which Andrew validates enthusiastically.4:14–7:16 · Andrew pushing back 0/10 Managing and Maintaining Text.run Andrew offers ideas on buying SaaS companies and suggests core growth levers like price increases. Tom agrees, laying out his top growth levers including organic directories and SEO optimization.7:17–9:43 · Andrew pushing back 1/10 Pricing Strategies and Lifetime Deals Andrew brings up the trade-offs of lifetime deals, highlighting the risk of ongoing support costs versus upfront cash. Tom responds with practical ways to mitigate risks by limiting upgrade periods and tiers.9:44–11:47 · Andrew pushing back 0/10 The Decision to Sell and Transition Andrew inquires about the decision to sell and the experience with buyers on Acquire.com. Tom explains his motivation to inject capital into his agency and describes how fast the sales closed.11:48–14:06 · Andrew pushing back 0/10 Acquisition Learnings and Leveraging AI Tom talks about utilizing AI to assist in due diligence and account handovers. Andrew shares Acquire.com internal best practices for prompting LLMs to review LOIs and evaluate acquisition offers.14:07–16:12 · Andrew pushing back 0/10 Advice for Prospective Startup Sellers Tom advises founders to use Acquire.com for seamless small transactions and describes his new agency focus. Andrew wraps up the interview on an amicable and supportive note.16:13–16:43 · Andrew pushing back 0/10 Podcast Conclusion and Acquire.com Information Standard promotional outro monologue read by the voiceover with no dialogue or debate.

speaking balance: gold is Andrew, purple is the guest (3 minute bins)

0:00 · Andrew 27.1% · guest 72.9%0:00 · Andrew 27.1% · guest 72.9%3:00 · Andrew 21.3% · guest 78.7%3:00 · Andrew 21.3% · guest 78.7%6:00 · Andrew 20.9% · guest 79.1%6:00 · Andrew 20.9% · guest 79.1%9:00 · Andrew 13.5% · guest 86.5%9:00 · Andrew 13.5% · guest 86.5%12:00 · Andrew 16.4% · guest 83.6%12:00 · Andrew 16.4% · guest 83.6%15:00 · Andrew 25.4% · guest 74.6%15:00 · Andrew 25.4% · guest 74.6%
Sharpest disagreement ▶ 8:14 Tom defends lifetime pricing with risk mitigation

In a very cordial discussion, Tom provides a nuanced counterpoint defending lifetime deals as viable if structured carefully to bound long-term support obligations.

 Hardest push from Andrew ▶ 7:50 Andrew presses on downside of lifetime deals

Andrew challenges the concept of lifetime deals, highlighting the burden of lifetime support versus one-time revenue.

 Biggest teaching moment ▶ 8:30 Tom outlines structure to de-risk lifetime deals

Tom educates on structuring lifetime pricing tiers specifically to limit feature upgrade terms and avoid unbounded maintenance commitments.

 Andrew holds their own ▶ 13:24 Andrew shares workflow for LLM-assisted deal review

Andrew demonstrates platform domain expertise by sharing how Acquire.com uses ChatGPT to review Letters of Intent and draft counteroffers.
the scores for every segment, with the reasoning behind each
ChapterTopicAndrew as informed peerGuest teachingGuest disagreementAndrew pushing backWhy
Meet Tom Ulman: Founder of Almost Human Digital 3300 Andrew prompts Tom on how he acquired waitlist.email and Text.run, and how he grew user engagement. Tom explains his strategy of eliminating free pricing tiers and learning from users, which Andrew validates enthusiastically.
Managing and Maintaining Text.run 4200 Andrew offers ideas on buying SaaS companies and suggests core growth levers like price increases. Tom agrees, laying out his top growth levers including organic directories and SEO optimization.
Pricing Strategies and Lifetime Deals 4301 Andrew brings up the trade-offs of lifetime deals, highlighting the risk of ongoing support costs versus upfront cash. Tom responds with practical ways to mitigate risks by limiting upgrade periods and tiers.
The Decision to Sell and Transition 2300 Andrew inquires about the decision to sell and the experience with buyers on Acquire.com. Tom explains his motivation to inject capital into his agency and describes how fast the sales closed.
Acquisition Learnings and Leveraging AI 5200 Tom talks about utilizing AI to assist in due diligence and account handovers. Andrew shares Acquire.com internal best practices for prompting LLMs to review LOIs and evaluate acquisition offers.
Advice for Prospective Startup Sellers 2200 Tom advises founders to use Acquire.com for seamless small transactions and describes his new agency focus. Andrew wraps up the interview on an amicable and supportive note.
Podcast Conclusion and Acquire.com Information 0000 Standard promotional outro monologue read by the voiceover with no dialogue or debate.

Statements from this episode (8)

Disclosure
Eliminating Waitlist.email's Free Tier Improved the Micro-SaaS Business
“Initially, the, had two pricing tiers. One was pre- And then there was a paid pricing tier, which was a monthly revenue, which enabled, you know, some AI features as well as adding custom metadata. So additional fields in collecting the data initially, rather …”
Tom Ulman Oct 14, 2025 ▶ 3:21
Disclosure
Ulman Offered Free Lifetime Pro Tiers for Product Feedback
“And then based, based on that, also reached out to kind of users and offered them free pro tier for life and also to try and get them to reach out. And that way I kind of learned what different features would be best and was able to kind process kickstart off …”
Tom Ulman Oct 14, 2025 ▶ 3:56
Insight
Organic Distribution Is the Primary Initial Growth Lever for Micro-SaaS
“I think just getting eyes on the product is probably the first growth lever to try and pull. And that way, you know, if the product's something people want, you'll organically get those customers to start coming through.”
Tom Ulman Oct 14, 2025 ▶ 6:04
Insight
Mitigate Lifetime SaaS Risks by Limiting Feature Upgrades to One Year
“One way to mitigate risk is to make sure that, you know, maybe it's a, maybe you create a specific tier for that lifetime plan, and maybe it covers it, you know, upgrades for a year, and then it's, you know, ongoing features, it separates it, so I think as lon…”
Tom Ulman Oct 14, 2025 ▶ 8:51
Insight
Lifetime Deals Drive Fast Revenue but Cause Heavy Support Burdens
“I think if it's kind of a make or break, or you want that really fast user base or revenue growth, then it's a really good lever to engage, but obviously it's not for everyone, and it doesn't always play out the way you want, and it can lead to, you know, mass…”
Tom Ulman Oct 14, 2025 ▶ 9:12
Disclosure
Ulman Received Inquiries and Deals Within Two Weeks on Acquire
“I had multiple buyers within the first couple of days, first week. I'd say the story is the same with both products I sold. It was yeah, immediately having people reaching out, asking questions, and I think yeah, both times within the space of a week or a coup…”
Tom Ulman Oct 14, 2025 ▶ 11:03
Insight
Minimal Due Diligence Accelerates Small Software Project Acquisitions
“Because I think because they're small projects, there wasn't a huge amount of due diligence, but so it made it really smooth and quick processes in both cases.”
Tom Ulman Oct 14, 2025 ▶ 11:37
Disclosure
Gazdecki: Acquire.com Uses ChatGPT to Review LOIs and Rate Offers
“We do it all the time at Acquire. When we have a letter of intent or we have an opinion of our own, but we want another one, you can just upload that in the chat to GBT and say, is there anything concerning here? How would you rate this out of a hundred? What'…”
Andrew Gazdecki Oct 14, 2025 ▶ 13:26
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