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Jan 2, 2024 · 21m · startup-acquisition-stories

Startup Acquisition Stories with Justin Vanderheide, Founder of Swimgen

Justin Vanderheide · 12m spoken Andrew Gazdecki · 6m spoken
0:00 / 0:00

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In this episode of Startup Acquisition Stories, host Andrew Gazdecki interviews entrepreneur Justin Vanderheide on how he bootstrapped, grew, and successfully sold two six-figure software businesses—Swimgen and a suite of Zendesk apps—on Acquire.com before pivoting to physical gym ownership. Justin shares actionable insights on niche vertical SaaS development, managing due diligence, selecting the right buyers, and executing smooth cross-border exits.

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 32.7% of the talking time here. How this is scored →

Andrew as informed peer 3.9 Guest teaching 2.0 Guest disagreement 0.0 Andrew pushing back 0.0
05100:0010:0020:000:24–3:46 · Andrew as informed peer 3/10 Meet Justin Vanderheide: Background and Dual Exits Andrew welcomes Justin warmly and highlights the appeal of automating manual workflows into software. Justin explains the origin of Swimgen during his time as a high school swim instructor.3:46–7:54 · Andrew as informed peer 4/10 Capitalizing on Zendesk's Sunsetted Free Apps Andrew offers observations on vertical SaaS and overlooked niche markets. Justin details how Zendesk sunsetting its free apps presented a clear business opportunity to build paid alternatives.7:55–10:16 · Andrew as informed peer 4/10 The Decision and Timing to Sell Both Businesses Andrew shares his perspective on the critical importance of exit timing, referencing rapid valuation drops in the AI sector. Justin explains how gym commitments and favorable currency exchange rates drove his exit decision.10:20–12:28 · Andrew as informed peer 4/10 Navigating Acquire.com and the Listing Process Andrew jokes about Acquire's SEO content strategy and identifies customer support team members. Justin describes refining his listing and managing inbound prospective buyers.12:28–16:35 · Andrew as informed peer 5/10 Selecting Distinct Buyers for Two Different Products Andrew offers M&A best practices, urging founders to treat all inquiries as potential buyers. Justin discusses tailoring buyer selection between a solo developer for Swimgen and an investment group for Zendesk apps.16:35–19:12 · Andrew as informed peer 5/10 Managing Due Diligence, Asset Transfers, and Transparency Andrew emphasizes that hidden issues kill acquisitions and counsels full transparency. Justin recounts navigating Canadian-to-US entity Stripe transfers and detecting anomalous API subscription metrics.19:12–21:00 · Andrew as informed peer 2/10 Transitioning to Physical Business at Steel Peak Climbing Andrew points out the stark contrast in capital requirements between software and brick-and-mortar gyms. Justin discusses founding Steel Peak Climbing and wrapping up his software ventures.0:24–3:46 · Guest teaching 2/10 Meet Justin Vanderheide: Background and Dual Exits Andrew welcomes Justin warmly and highlights the appeal of automating manual workflows into software. Justin explains the origin of Swimgen during his time as a high school swim instructor.3:46–7:54 · Guest teaching 2/10 Capitalizing on Zendesk's Sunsetted Free Apps Andrew offers observations on vertical SaaS and overlooked niche markets. Justin details how Zendesk sunsetting its free apps presented a clear business opportunity to build paid alternatives.7:55–10:16 · Guest teaching 2/10 The Decision and Timing to Sell Both Businesses Andrew shares his perspective on the critical importance of exit timing, referencing rapid valuation drops in the AI sector. Justin explains how gym commitments and favorable currency exchange rates drove his exit decision.10:20–12:28 · Guest teaching 2/10 Navigating Acquire.com and the Listing Process Andrew jokes about Acquire's SEO content strategy and identifies customer support team members. Justin describes refining his listing and managing inbound prospective buyers.12:28–16:35 · Guest teaching 2/10 Selecting Distinct Buyers for Two Different Products Andrew offers M&A best practices, urging founders to treat all inquiries as potential buyers. Justin discusses tailoring buyer selection between a solo developer for Swimgen and an investment group for Zendesk apps.16:35–19:12 · Guest teaching 3/10 Managing Due Diligence, Asset Transfers, and Transparency Andrew emphasizes that hidden issues kill acquisitions and counsels full transparency. Justin recounts navigating Canadian-to-US entity Stripe transfers and detecting anomalous API subscription metrics.19:12–21:00 · Guest teaching 1/10 Transitioning to Physical Business at Steel Peak Climbing Andrew points out the stark contrast in capital requirements between software and brick-and-mortar gyms. Justin discusses founding Steel Peak Climbing and wrapping up his software ventures.0:24–3:46 · Guest disagreement 0/10 Meet Justin Vanderheide: Background and Dual Exits Andrew welcomes Justin warmly and highlights the appeal of automating manual workflows into software. Justin explains the origin of Swimgen during his time as a high school swim instructor.3:46–7:54 · Guest disagreement 0/10 Capitalizing on Zendesk's Sunsetted Free Apps Andrew offers observations on vertical SaaS and overlooked niche markets. Justin details how Zendesk sunsetting its free apps presented a clear business opportunity to build paid alternatives.7:55–10:16 · Guest disagreement 0/10 The Decision and Timing to Sell Both Businesses Andrew shares his perspective on the critical importance of exit timing, referencing rapid valuation drops in the AI sector. Justin explains how gym commitments and favorable currency exchange rates drove his exit decision.10:20–12:28 · Guest disagreement 0/10 Navigating Acquire.com and the Listing Process Andrew jokes about Acquire's SEO content strategy and identifies customer support team members. Justin describes refining his listing and managing inbound prospective buyers.12:28–16:35 · Guest disagreement 0/10 Selecting Distinct Buyers for Two Different Products Andrew offers M&A best practices, urging founders to treat all inquiries as potential buyers. Justin discusses tailoring buyer selection between a solo developer for Swimgen and an investment group for Zendesk apps.16:35–19:12 · Guest disagreement 0/10 Managing Due Diligence, Asset Transfers, and Transparency Andrew emphasizes that hidden issues kill acquisitions and counsels full transparency. Justin recounts navigating Canadian-to-US entity Stripe transfers and detecting anomalous API subscription metrics.19:12–21:00 · Guest disagreement 0/10 Transitioning to Physical Business at Steel Peak Climbing Andrew points out the stark contrast in capital requirements between software and brick-and-mortar gyms. Justin discusses founding Steel Peak Climbing and wrapping up his software ventures.0:24–3:46 · Andrew pushing back 0/10 Meet Justin Vanderheide: Background and Dual Exits Andrew welcomes Justin warmly and highlights the appeal of automating manual workflows into software. Justin explains the origin of Swimgen during his time as a high school swim instructor.3:46–7:54 · Andrew pushing back 0/10 Capitalizing on Zendesk's Sunsetted Free Apps Andrew offers observations on vertical SaaS and overlooked niche markets. Justin details how Zendesk sunsetting its free apps presented a clear business opportunity to build paid alternatives.7:55–10:16 · Andrew pushing back 0/10 The Decision and Timing to Sell Both Businesses Andrew shares his perspective on the critical importance of exit timing, referencing rapid valuation drops in the AI sector. Justin explains how gym commitments and favorable currency exchange rates drove his exit decision.10:20–12:28 · Andrew pushing back 0/10 Navigating Acquire.com and the Listing Process Andrew jokes about Acquire's SEO content strategy and identifies customer support team members. Justin describes refining his listing and managing inbound prospective buyers.12:28–16:35 · Andrew pushing back 0/10 Selecting Distinct Buyers for Two Different Products Andrew offers M&A best practices, urging founders to treat all inquiries as potential buyers. Justin discusses tailoring buyer selection between a solo developer for Swimgen and an investment group for Zendesk apps.16:35–19:12 · Andrew pushing back 0/10 Managing Due Diligence, Asset Transfers, and Transparency Andrew emphasizes that hidden issues kill acquisitions and counsels full transparency. Justin recounts navigating Canadian-to-US entity Stripe transfers and detecting anomalous API subscription metrics.19:12–21:00 · Andrew pushing back 0/10 Transitioning to Physical Business at Steel Peak Climbing Andrew points out the stark contrast in capital requirements between software and brick-and-mortar gyms. Justin discusses founding Steel Peak Climbing and wrapping up his software ventures.

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

0:00 · Andrew 27.6% · guest 72.4%0:00 · Andrew 27.6% · guest 72.4%3:00 · Andrew 24.6% · guest 75.4%3:00 · Andrew 24.6% · guest 75.4%6:00 · Andrew 28.6% · guest 71.4%6:00 · Andrew 28.6% · guest 71.4%9:00 · Andrew 38.3% · guest 61.7%9:00 · Andrew 38.3% · guest 61.7%12:00 · Andrew 34.2% · guest 65.8%12:00 · Andrew 34.2% · guest 65.8%15:00 · Andrew 45% · guest 55%15:00 · Andrew 45% · guest 55%18:00 · Andrew 35.8% · guest 64.2%18:00 · Andrew 35.8% · guest 64.2%21:00 · Andrew 1.1% · guest 98.9%21:00 · Andrew 1.1% · guest 98.9%
Sharpest disagreement ▶ 15:23 Independent seller perspective

In a completely amicable interview, Justin playfully clarifies that his strategy of taking every buyer call came from personal trial rather than advice from Andrew's team.

 Hardest push from Andrew ▶ 15:23 Inquiring about advisory origin

Andrew probes whether Justin's advice originated from the Acquire advisory staff before accepting Justin's independent perspective.

 Biggest teaching moment ▶ 16:51 Cross-border asset transfer hurdles

Justin explains the practical technical and legal complications of migrating Canadian Stripe accounts and legacy AWS accounts to US buyers during due diligence.

 Andrew holds their own ▶ 18:43 Advising total transparency in M&A

Andrew demonstrates industry expertise by detailing how unexpected disclosures during due diligence destroy buyer trust and collapse deals.
the scores for every segment, with the reasoning behind each
ChapterTopicAndrew as informed peerGuest teachingGuest disagreementAndrew pushing backWhy
Meet Justin Vanderheide: Background and Dual Exits 3200 Andrew welcomes Justin warmly and highlights the appeal of automating manual workflows into software. Justin explains the origin of Swimgen during his time as a high school swim instructor.
Capitalizing on Zendesk's Sunsetted Free Apps 4200 Andrew offers observations on vertical SaaS and overlooked niche markets. Justin details how Zendesk sunsetting its free apps presented a clear business opportunity to build paid alternatives.
The Decision and Timing to Sell Both Businesses 4200 Andrew shares his perspective on the critical importance of exit timing, referencing rapid valuation drops in the AI sector. Justin explains how gym commitments and favorable currency exchange rates drove his exit decision.
Navigating Acquire.com and the Listing Process 4200 Andrew jokes about Acquire's SEO content strategy and identifies customer support team members. Justin describes refining his listing and managing inbound prospective buyers.
Selecting Distinct Buyers for Two Different Products 5200 Andrew offers M&A best practices, urging founders to treat all inquiries as potential buyers. Justin discusses tailoring buyer selection between a solo developer for Swimgen and an investment group for Zendesk apps.
Managing Due Diligence, Asset Transfers, and Transparency 5300 Andrew emphasizes that hidden issues kill acquisitions and counsels full transparency. Justin recounts navigating Canadian-to-US entity Stripe transfers and detecting anomalous API subscription metrics.
Transitioning to Physical Business at Steel Peak Climbing 2100 Andrew points out the stark contrast in capital requirements between software and brick-and-mortar gyms. Justin discusses founding Steel Peak Climbing and wrapping up his software ventures.

Statements from this episode (12)

Assertion Not checkable as stated
Vanderheide Bootstrapped Swimgen to Serve Every YMCA in Canada
“Sort of just bootstrapped it with that, that first customer and through word of mouth, like every YMCA in Canada was publishing on this along with, you know, municipalities, military bases, what have you. And so we grew from like one customer to hundreds of po…”
Justin Vanderheide Jan 2, 2024 ▶ 3:02
Disclosure
Vanderheide Recreated Sunsetted Zendesk Apps for One Dollar Per Agent Monthly
“So I recreated a bunch of the apps that had been available for free nominal price of, you know, one dollar per support agent per month and managed to get those out really quick.”
Justin Vanderheide Jan 2, 2024 ▶ 4:45
Opinion
Gazdecki: Boring Vertical SaaS Markets Are Massively Overlooked
“Boring industries like pools, you know, those are massively overlooked markets that are big and have a lot of opportunity in it.”
Andrew Gazdecki Jan 2, 2024 ▶ 7:08
Assertion Not checkable as stated
Gazdecki: AI Startups Valued in the Millions Are Now Worth Zero
“I've seen a number of different businesses, like, AI companies is probably a good example for if you sold them eight months ago worth millions and then now zero, like absolutely zero.”
Andrew Gazdecki Jan 2, 2024 ▶ 9:46
Insight
Vanderheide: Answering Early Buyer Questions Progressively Improves M&A Data Packages
“People had a lot of questions, but anytime you go digging and you answer their questions, you know, you just put that with all the other data and then for any future folks that come along, it's there. And so the data you have available for people, you know, ju…”
Justin Vanderheide Jan 2, 2024 ▶ 11:59
Disclosure
Vanderheide Rejected Private Equity Offers to Sell Swimgen to Solo Developer
“Yeah, for SwimGen, I felt quite strongly about making sure the right person was taking it on, and so the private equity firms, family offices, the more businessy folks, I was shying away from a little bit. In the end, I did sell it to sort of like passionate, …”
Justin Vanderheide Jan 2, 2024 ▶ 12:56
Disclosure
Vanderheide Sold Zendesk Apps Portfolio to an Investor Aggregator Group
“On the Zendesk side of things, I didn't feel as passionately that it had to be, you know, passionate solo dev. And so that one went to like a group of investors that are just scooping up a bunch of smaller, smaller apps and things like that.”
Justin Vanderheide Jan 2, 2024 ▶ 13:28
Insight
Vanderheide: Founders Should Provide Granular Raw Data in Acquisition Listings
“Over explain everything in your listing. There's not going to be too much data available to people. So, you know, if you've got the exact, you know, monthly data points of visits, revenue, everything like they can break it out and look at it however they want.…”
Justin Vanderheide Jan 2, 2024 ▶ 14:31
Insight
Vanderheide: Selling Founders Should Accept Almost Every Buyer Call Request
“I'd say pretty well every request for a face-to-face call, and I wouldn't be too choosy unless you're overwhelmingly busy. You never know what's going to come out of that discussion face-to-face. I maybe only had one that was like really not productive and sho…”
Justin Vanderheide Jan 2, 2024 ▶ 14:59
Insight
Gazdecki: Treat Every M&A Prospect as an Active Buyer Until Rejected
“Assume everyone is the buyer until they're not, until they say they're not interested, continue to follow up, continue to push for calls. And that's really like the biggest part with acquisitions that a lot of people I think miss is number one, you gotta be ob…”
Andrew Gazdecki Jan 2, 2024 ▶ 15:41
Assertion Supported
Vanderheide: US-Canada Acquisitions Cannot Directly Transfer Stripe Accounts
“Because I was Canadian, getting acquired by American companies, we couldn't just transfer the Stripe account because it's, like, set as a Canadian entity type thing, so we had to actually, like, switch over Stripe keys and stuff, which wasn't as seamless, but …”
Justin Vanderheide Jan 2, 2024 ▶ 17:11
Insight
Vanderheide: Never Hide Flaws; Share Raw Data Upfront in Due Diligence
“Don't try to, like, hide things, it'll, it'll come out in due diligence, so I'm just in that initial data dump, like I said, over-explain, just post all the raw data, even if you've got it, and they can look at it as is.”
Justin Vanderheide Jan 2, 2024 ▶ 18:24
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