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Nov 15, 2021 · 20m · startup-acquisition-stories

Startup Acquisition Stories with Daniel Jakaitis Founder of Chatkick

Daniel Jekaitis · 11m spoken Andrew Gazdecki · 6m 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 SaaS Acquisition Stories, host Andrew Gazdecki interviews Chatkick founder Daniel Jakaitis about his strategic acquisition of Trinsley on MicroAcquire. Daniel shares actionable insights on sourcing complementary add-on software, structuring hybrid cash-and-equity deals, conducting rigorous technical due diligence, and managing asset transfers.

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 32.5% of the talking time here. How this is scored →

Andrew as informed peer 3.4 Guest teaching 2.4 Guest disagreement 0.4 Andrew pushing back 0.0
05100:0010:0020:000:24–5:42 · Andrew as informed peer 3/10 Meet Daniel Jakaitis: Engineering Background and Early Career The conversation is very friendly and conversational. Daniel explains his background and clarifies a key product nuance between sales sequencing and recruiting tools regarding corporate versus personal email targeting.5:43–7:45 · Andrew as informed peer 3/10 Structuring a Hybrid Cash and Equity Deal Daniel details his hybrid cash and equity structure designed to bridge the valuation gap and keep the seller invested in post-close support, which Andrew enthusiastically validates.7:46–12:56 · Andrew as informed peer 5/10 Technical Due Diligence and Code Review Strategy Andrew demonstrates real startup sale experience by bringing up Black Duck license audits, while Daniel explains practical code review heuristics for non-technical and technical buyers.12:56–15:56 · Andrew as informed peer 4/10 Asset Transfer Execution and Escrow Navigation Daniel discusses escrow delays and password transfer best practices using 1Password, while Andrew relates the escrow pain point to upcoming MicroAcquire product features.15:58–20:30 · Andrew as informed peer 2/10 The Importance of Interpersonal Trust and Speed The segment covers closing advice on transaction velocity and interpersonal trust, followed by rapid-fire questions regarding influences and book recommendations.0:24–5:42 · Guest teaching 3/10 Meet Daniel Jakaitis: Engineering Background and Early Career The conversation is very friendly and conversational. Daniel explains his background and clarifies a key product nuance between sales sequencing and recruiting tools regarding corporate versus personal email targeting.5:43–7:45 · Guest teaching 2/10 Structuring a Hybrid Cash and Equity Deal Daniel details his hybrid cash and equity structure designed to bridge the valuation gap and keep the seller invested in post-close support, which Andrew enthusiastically validates.7:46–12:56 · Guest teaching 4/10 Technical Due Diligence and Code Review Strategy Andrew demonstrates real startup sale experience by bringing up Black Duck license audits, while Daniel explains practical code review heuristics for non-technical and technical buyers.12:56–15:56 · Guest teaching 2/10 Asset Transfer Execution and Escrow Navigation Daniel discusses escrow delays and password transfer best practices using 1Password, while Andrew relates the escrow pain point to upcoming MicroAcquire product features.15:58–20:30 · Guest teaching 1/10 The Importance of Interpersonal Trust and Speed The segment covers closing advice on transaction velocity and interpersonal trust, followed by rapid-fire questions regarding influences and book recommendations.0:24–5:42 · Guest disagreement 1/10 Meet Daniel Jakaitis: Engineering Background and Early Career The conversation is very friendly and conversational. Daniel explains his background and clarifies a key product nuance between sales sequencing and recruiting tools regarding corporate versus personal email targeting.5:43–7:45 · Guest disagreement 0/10 Structuring a Hybrid Cash and Equity Deal Daniel details his hybrid cash and equity structure designed to bridge the valuation gap and keep the seller invested in post-close support, which Andrew enthusiastically validates.7:46–12:56 · Guest disagreement 1/10 Technical Due Diligence and Code Review Strategy Andrew demonstrates real startup sale experience by bringing up Black Duck license audits, while Daniel explains practical code review heuristics for non-technical and technical buyers.12:56–15:56 · Guest disagreement 0/10 Asset Transfer Execution and Escrow Navigation Daniel discusses escrow delays and password transfer best practices using 1Password, while Andrew relates the escrow pain point to upcoming MicroAcquire product features.15:58–20:30 · Guest disagreement 0/10 The Importance of Interpersonal Trust and Speed The segment covers closing advice on transaction velocity and interpersonal trust, followed by rapid-fire questions regarding influences and book recommendations.0:24–5:42 · Andrew pushing back 0/10 Meet Daniel Jakaitis: Engineering Background and Early Career The conversation is very friendly and conversational. Daniel explains his background and clarifies a key product nuance between sales sequencing and recruiting tools regarding corporate versus personal email targeting.5:43–7:45 · Andrew pushing back 0/10 Structuring a Hybrid Cash and Equity Deal Daniel details his hybrid cash and equity structure designed to bridge the valuation gap and keep the seller invested in post-close support, which Andrew enthusiastically validates.7:46–12:56 · Andrew pushing back 0/10 Technical Due Diligence and Code Review Strategy Andrew demonstrates real startup sale experience by bringing up Black Duck license audits, while Daniel explains practical code review heuristics for non-technical and technical buyers.12:56–15:56 · Andrew pushing back 0/10 Asset Transfer Execution and Escrow Navigation Daniel discusses escrow delays and password transfer best practices using 1Password, while Andrew relates the escrow pain point to upcoming MicroAcquire product features.15:58–20:30 · Andrew pushing back 0/10 The Importance of Interpersonal Trust and Speed The segment covers closing advice on transaction velocity and interpersonal trust, followed by rapid-fire questions regarding influences and book recommendations.

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

0:00 · Andrew 41.3% · guest 58.7%0:00 · Andrew 41.3% · guest 58.7%3:00 · Andrew 34.7% · guest 65.3%3:00 · Andrew 34.7% · guest 65.3%6:00 · Andrew 27.2% · guest 72.8%6:00 · Andrew 27.2% · guest 72.8%9:00 · Andrew 37.8% · guest 62.2%9:00 · Andrew 37.8% · guest 62.2%12:00 · Andrew 20.1% · guest 79.9%12:00 · Andrew 20.1% · guest 79.9%15:00 · Andrew 40.4% · guest 59.6%15:00 · Andrew 40.4% · guest 59.6%18:00 · Andrew 26% · guest 74%18:00 · Andrew 26% · guest 74%
Sharpest disagreement ▶ 5:00 Correction on personal versus corporate email outreach

In a very collaborative interview, Daniel offers a mild contrarian clarification on how recruiting automation differs fundamentally from sales tools.

 Hardest push from Andrew ▶ 1:32 Playful challenge on developer tech stack history

Andrew jokingly quizzes the guest on PHP version 1 to gauge his engineering background before pivoting into the acquisition story.

 Biggest teaching moment ▶ 9:45 Clarifying MIT versus GPL licensing traps

When Andrew misremembers whether MIT or GPL is the open-source license that causes acquisition diligence problems, Daniel immediately clarifies that MIT is safe while GPL poses commercial risks.

 Andrew holds their own ▶ 9:20 Andrew recounts past Black Duck audit experience

Andrew shares firsthand knowledge of acquisition diligence by recounting how a Black Duck audit delayed the sale of his first company due to open-source licensing.
the scores for every segment, with the reasoning behind each
ChapterTopicAndrew as informed peerGuest teachingGuest disagreementAndrew pushing backWhy
Meet Daniel Jakaitis: Engineering Background and Early Career 3310 The conversation is very friendly and conversational. Daniel explains his background and clarifies a key product nuance between sales sequencing and recruiting tools regarding corporate versus personal email targeting.
Structuring a Hybrid Cash and Equity Deal 3200 Daniel details his hybrid cash and equity structure designed to bridge the valuation gap and keep the seller invested in post-close support, which Andrew enthusiastically validates.
Technical Due Diligence and Code Review Strategy 5410 Andrew demonstrates real startup sale experience by bringing up Black Duck license audits, while Daniel explains practical code review heuristics for non-technical and technical buyers.
Asset Transfer Execution and Escrow Navigation 4200 Daniel discusses escrow delays and password transfer best practices using 1Password, while Andrew relates the escrow pain point to upcoming MicroAcquire product features.
The Importance of Interpersonal Trust and Speed 2100 The segment covers closing advice on transaction velocity and interpersonal trust, followed by rapid-fire questions regarding influences and book recommendations.

Statements from this episode (9)

Assertion Supported
Gazdecki: Daniel Jekaitis Acquired Startup on MicroAcquire for Around $250,000
“You recently acquired a startup at Microquire for around a quarter million, and you were telling me you bought something else as well”
Andrew Gazdecki Nov 15, 2021 ▶ 0:44
Disclosure
Daniel Jekaitis: Chatkick acquired Trinsley after finding it on MicroAcquire
“In, in late April, I think it was I saw the Trinsley product, which we ended up acquiring come onto the market on the platform. And I immediately reached out to the founder, David.”
Daniel Jekaitis Nov 15, 2021 ▶ 3:22
Disclosure
Jakaitis: Trinsley was originally listed at a $350,000 asking price
“So originally I think it was listed at 350,000 asking the price.”
Daniel Jekaitis Nov 15, 2021 ▶ 5:55
Disclosure
Chatkick Met 60-70% of Trinsley's Cash Asking Price Plus Equity
“So we gave him a nice tranche of cash. I would say we got to about the 60, 70% range of his cash expectations. And then I would say a healthy block of equity that if there is an exit event, he's gonna see some very nice returns off of it.”
Daniel Jekaitis Nov 15, 2021 ▶ 7:02
Insight
Jakaitis: Giving sellers equity ensures responsive post-acquisition technical support
“There's no matter how technical you are and how much into the weed that the product you can get, there's always like little corner cases that you'll want to ping him about. And because he has skin in the game today, he's always willing to pick up the phone and…”
Daniel Jekaitis Nov 15, 2021 ▶ 7:30
Insight
Jakaitis: Consistency of folder structure is the top heuristic in code reviews
“For me the biggest heuristic that I go off of is organization and consistency of structure. So it's really hard if you're just, like, eyeballing, like, Thousands of lines of code over a zoom or whatever it is to figure out if it's quality code. But what you ca…”
Daniel Jekaitis Nov 15, 2021 ▶ 11:22
Insight
Jakaitis: Unupdated dependencies from 2-3 years ago are major diligence red flags
“Big red flags if they're like on versions that are outdated like two, three years ago, and it's very clear they've never updated it. I know I went into diligence with a couple of different products that never ended up closing because you'd get in there and the…”
Daniel Jekaitis Nov 15, 2021 ▶ 12:19
Assertion Not checkable as stated
Jakaitis: Chatkick Faced Escrow.com Payment Delays Up to Three Weeks
“Like, we used escrow.com for our payments, and we had all sorts of issues getting payments into the platform, and then also out like, delays up to two to three weeks, which was, Challenging because you want to impart trust on each other, but at the same time, …”
Daniel Jekaitis Nov 15, 2021 ▶ 13:40
Insight
Jakaitis: Hand Over SaaS Assets via 1Password and Immediately Rotate 2FA
“Put everything in like a OnePass account and then just hand over the keys to the OnePass account. And then wash your hands of it, right? And my recommendation as like a buyer, right? Like when you get your hands on all that, roll the passwords, make sure you c…”
Daniel Jekaitis Nov 15, 2021 ▶ 14:20
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