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Nov 16, 2021 · 26m · startup-acquisition-stories

Startup Acquisition Stories with Derek Homann Co-founder of Workshop

Derek Homann · 16m spoken Andrew Gazdecki · 5m spoken
0:00 / 0:00

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In this episode of SaaS Acquisition Stories, MicroAcquire CEO Andrew Gazdecki interviews Workshop co-founder Derek Homann about bootstrapping, licensing, and successfully exiting his co-browsing startup, Median. Derek shares practical insights on managing deal flow, defining founder non-negotiables, navigating due diligence, and leveraging an initial acquisition into a venture-backed enterprise.

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 24.9% of the talking time here. How this is scored →

Andrew as informed peer 2.9 Guest teaching 1.0 Guest disagreement 0.0 Andrew pushing back 0.1
05100:0010:0020:000:24–6:17 · Andrew as informed peer 1/10 Derek Homann's Acquisition and Celebratory Purchase Andrew opens with casual questions about Derek's acquisition and celebratory purchase. Derek explains Median's bootstrapping history and how they executed non-exclusive perpetual licensing deals before listing on MicroAcquire.6:19–8:49 · Andrew as informed peer 1/10 Navigating the MicroAcquire Deal Flow and Timeline Derek outlines his exact timeline on MicroAcquire from 40 inquiries to 10 Zoom calls and an LOI in a week and a half. Andrew primarily listens without pushing back.8:49–12:51 · Andrew as informed peer 3/10 Key Advice on Founder Objectives and Non-Negotiables Andrew connects Derek's approach of prioritizing clean deal terms over top price to his own experience selling Bizness Apps. Derek emphasizes knowing non-negotiables and having a prepared data room.12:51–15:28 · Andrew as informed peer 4/10 Managing Diligence Hurdles and Contract Obligations Derek shares difficulties in assessing existing customer contract obligations during due diligence. Andrew contributes proprietary MicroAcquire platform data showing connected analytics tools increase buyer inquiries by 500%.15:28–18:54 · Andrew as informed peer 3/10 Launching Workshop and Transitioning to Venture Capital Derek describes launching Workshop as a venture-backed startup with former Flywheel teammates after banking nearly $2M total across deals. Andrew mirrors this path with his own shift from bootstrapped founder to VC-backed operator.18:54–23:41 · Andrew as informed peer 3/10 Admired Entrepreneurs and Collaborative Influences Andrew asks Derek for admired entrepreneurs while playfully barring Elon Musk as an option. Andrew explains how Derek's successful sale was the defining proof-of-concept milestone for MicroAcquire.23:42–25:42 · Andrew as informed peer 5/10 Recommended Resources for Sales and Entrepreneurship When Derek mentions looking into sales books, Andrew identifies Mark Roberge's 'The Sales Acceleration Formula' and recommends additional entrepreneurship titles by Daniel Pink, Jason Lemkin, and Aaron Ross.0:24–6:17 · Guest teaching 2/10 Derek Homann's Acquisition and Celebratory Purchase Andrew opens with casual questions about Derek's acquisition and celebratory purchase. Derek explains Median's bootstrapping history and how they executed non-exclusive perpetual licensing deals before listing on MicroAcquire.6:19–8:49 · Guest teaching 1/10 Navigating the MicroAcquire Deal Flow and Timeline Derek outlines his exact timeline on MicroAcquire from 40 inquiries to 10 Zoom calls and an LOI in a week and a half. Andrew primarily listens without pushing back.8:49–12:51 · Guest teaching 2/10 Key Advice on Founder Objectives and Non-Negotiables Andrew connects Derek's approach of prioritizing clean deal terms over top price to his own experience selling Bizness Apps. Derek emphasizes knowing non-negotiables and having a prepared data room.12:51–15:28 · Guest teaching 1/10 Managing Diligence Hurdles and Contract Obligations Derek shares difficulties in assessing existing customer contract obligations during due diligence. Andrew contributes proprietary MicroAcquire platform data showing connected analytics tools increase buyer inquiries by 500%.15:28–18:54 · Guest teaching 1/10 Launching Workshop and Transitioning to Venture Capital Derek describes launching Workshop as a venture-backed startup with former Flywheel teammates after banking nearly $2M total across deals. Andrew mirrors this path with his own shift from bootstrapped founder to VC-backed operator.18:54–23:41 · Guest teaching 0/10 Admired Entrepreneurs and Collaborative Influences Andrew asks Derek for admired entrepreneurs while playfully barring Elon Musk as an option. Andrew explains how Derek's successful sale was the defining proof-of-concept milestone for MicroAcquire.23:42–25:42 · Guest teaching 0/10 Recommended Resources for Sales and Entrepreneurship When Derek mentions looking into sales books, Andrew identifies Mark Roberge's 'The Sales Acceleration Formula' and recommends additional entrepreneurship titles by Daniel Pink, Jason Lemkin, and Aaron Ross.0:24–6:17 · Guest disagreement 0/10 Derek Homann's Acquisition and Celebratory Purchase Andrew opens with casual questions about Derek's acquisition and celebratory purchase. Derek explains Median's bootstrapping history and how they executed non-exclusive perpetual licensing deals before listing on MicroAcquire.6:19–8:49 · Guest disagreement 0/10 Navigating the MicroAcquire Deal Flow and Timeline Derek outlines his exact timeline on MicroAcquire from 40 inquiries to 10 Zoom calls and an LOI in a week and a half. Andrew primarily listens without pushing back.8:49–12:51 · Guest disagreement 0/10 Key Advice on Founder Objectives and Non-Negotiables Andrew connects Derek's approach of prioritizing clean deal terms over top price to his own experience selling Bizness Apps. Derek emphasizes knowing non-negotiables and having a prepared data room.12:51–15:28 · Guest disagreement 0/10 Managing Diligence Hurdles and Contract Obligations Derek shares difficulties in assessing existing customer contract obligations during due diligence. Andrew contributes proprietary MicroAcquire platform data showing connected analytics tools increase buyer inquiries by 500%.15:28–18:54 · Guest disagreement 0/10 Launching Workshop and Transitioning to Venture Capital Derek describes launching Workshop as a venture-backed startup with former Flywheel teammates after banking nearly $2M total across deals. Andrew mirrors this path with his own shift from bootstrapped founder to VC-backed operator.18:54–23:41 · Guest disagreement 0/10 Admired Entrepreneurs and Collaborative Influences Andrew asks Derek for admired entrepreneurs while playfully barring Elon Musk as an option. Andrew explains how Derek's successful sale was the defining proof-of-concept milestone for MicroAcquire.23:42–25:42 · Guest disagreement 0/10 Recommended Resources for Sales and Entrepreneurship When Derek mentions looking into sales books, Andrew identifies Mark Roberge's 'The Sales Acceleration Formula' and recommends additional entrepreneurship titles by Daniel Pink, Jason Lemkin, and Aaron Ross.0:24–6:17 · Andrew pushing back 0/10 Derek Homann's Acquisition and Celebratory Purchase Andrew opens with casual questions about Derek's acquisition and celebratory purchase. Derek explains Median's bootstrapping history and how they executed non-exclusive perpetual licensing deals before listing on MicroAcquire.6:19–8:49 · Andrew pushing back 0/10 Navigating the MicroAcquire Deal Flow and Timeline Derek outlines his exact timeline on MicroAcquire from 40 inquiries to 10 Zoom calls and an LOI in a week and a half. Andrew primarily listens without pushing back.8:49–12:51 · Andrew pushing back 0/10 Key Advice on Founder Objectives and Non-Negotiables Andrew connects Derek's approach of prioritizing clean deal terms over top price to his own experience selling Bizness Apps. Derek emphasizes knowing non-negotiables and having a prepared data room.12:51–15:28 · Andrew pushing back 0/10 Managing Diligence Hurdles and Contract Obligations Derek shares difficulties in assessing existing customer contract obligations during due diligence. Andrew contributes proprietary MicroAcquire platform data showing connected analytics tools increase buyer inquiries by 500%.15:28–18:54 · Andrew pushing back 0/10 Launching Workshop and Transitioning to Venture Capital Derek describes launching Workshop as a venture-backed startup with former Flywheel teammates after banking nearly $2M total across deals. Andrew mirrors this path with his own shift from bootstrapped founder to VC-backed operator.18:54–23:41 · Andrew pushing back 1/10 Admired Entrepreneurs and Collaborative Influences Andrew asks Derek for admired entrepreneurs while playfully barring Elon Musk as an option. Andrew explains how Derek's successful sale was the defining proof-of-concept milestone for MicroAcquire.23:42–25:42 · Andrew pushing back 0/10 Recommended Resources for Sales and Entrepreneurship When Derek mentions looking into sales books, Andrew identifies Mark Roberge's 'The Sales Acceleration Formula' and recommends additional entrepreneurship titles by Daniel Pink, Jason Lemkin, and Aaron Ross.

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

0:00 · Andrew 17.6% · guest 82.4%0:00 · Andrew 17.6% · guest 82.4%3:00 · Andrew 0.4% · guest 99.6%3:00 · Andrew 0.4% · guest 99.6%6:00 · Andrew 17.8% · guest 82.2%6:00 · Andrew 17.8% · guest 82.2%9:00 · Andrew 25% · guest 75%9:00 · Andrew 25% · guest 75%12:00 · Andrew 24.7% · guest 75.3%12:00 · Andrew 24.7% · guest 75.3%15:00 · Andrew 28.3% · guest 71.7%15:00 · Andrew 28.3% · guest 71.7%18:00 · Andrew 48.5% · guest 51.5%18:00 · Andrew 48.5% · guest 51.5%21:00 · Andrew 35.7% · guest 64.3%21:00 · Andrew 35.7% · guest 64.3%24:00 · Andrew 26.7% · guest 73.3%24:00 · Andrew 26.7% · guest 73.3%
Sharpest disagreement ▶ 0:24 Derek clarifies his executive title

In an otherwise completely harmonious interview, Derek immediately and politely corrects Andrew's assumption that he is CEO by stating he is co-founder and Chief Customer Officer.

 Hardest push from Andrew ▶ 31:35 Andrew preemptively bans Elon Musk answer

Andrew sets an explicit constraint on the guest's response by disallowing Elon Musk, explaining that past guests relied on that answer too frequently.

 Biggest teaching moment ▶ 3:00 Derek explains perpetual white-label licensing

Derek explains an uncommon bootstrap monetisation strategy involving selling non-exclusive perpetual enterprise licenses that served as substantial liquidity events prior to the company sale.

 Andrew holds their own ▶ 24:50 Andrew cites specific sales methodology titles and authors

Andrew demonstrates his domain expertise by identifying Mark Roberge's book when Derek forgets the exact title and recommending targeted founder resources by Jason Lemkin and Aaron Ross.
the scores for every segment, with the reasoning behind each
ChapterTopicAndrew as informed peerGuest teachingGuest disagreementAndrew pushing backWhy
Derek Homann's Acquisition and Celebratory Purchase 1200 Andrew opens with casual questions about Derek's acquisition and celebratory purchase. Derek explains Median's bootstrapping history and how they executed non-exclusive perpetual licensing deals before listing on MicroAcquire.
Navigating the MicroAcquire Deal Flow and Timeline 1100 Derek outlines his exact timeline on MicroAcquire from 40 inquiries to 10 Zoom calls and an LOI in a week and a half. Andrew primarily listens without pushing back.
Key Advice on Founder Objectives and Non-Negotiables 3200 Andrew connects Derek's approach of prioritizing clean deal terms over top price to his own experience selling Bizness Apps. Derek emphasizes knowing non-negotiables and having a prepared data room.
Managing Diligence Hurdles and Contract Obligations 4100 Derek shares difficulties in assessing existing customer contract obligations during due diligence. Andrew contributes proprietary MicroAcquire platform data showing connected analytics tools increase buyer inquiries by 500%.
Launching Workshop and Transitioning to Venture Capital 3100 Derek describes launching Workshop as a venture-backed startup with former Flywheel teammates after banking nearly $2M total across deals. Andrew mirrors this path with his own shift from bootstrapped founder to VC-backed operator.
Admired Entrepreneurs and Collaborative Influences 3001 Andrew asks Derek for admired entrepreneurs while playfully barring Elon Musk as an option. Andrew explains how Derek's successful sale was the defining proof-of-concept milestone for MicroAcquire.
Recommended Resources for Sales and Entrepreneurship 5000 When Derek mentions looking into sales books, Andrew identifies Mark Roberge's 'The Sales Acceleration Formula' and recommends additional entrepreneurship titles by Daniel Pink, Jason Lemkin, and Aaron Ross.

Statements from this episode (8)

Disclosure
Homann: Sold Median on MicroAcquire for just under $300,000
“Yeah, a little more than that. Just under a 300 day.”
Derek Homann Nov 16, 2021 ▶ 0:42
Disclosure
Homann: Median structured perpetual licensing deals to secure large checks
“We ended up doing this kind of non-exclusive perpetual licensing deal with them rather than doing a monthly subscription. And because we're a bootstrap company, we had the freedom to just take one really big check. And then basically hand over a copy of our co…”
Derek Homann Nov 16, 2021 ▶ 3:40
Assertion Not checkable as stated
Homann: Median secured an LOI within ten days of listing
“So I ran a pretty tight process there, and within a week and a half, we had an LOI in hand”
Derek Homann Nov 16, 2021 ▶ 7:47
Disclosure
Homann: Optimized Median sale for transition speed over highest purchase price
“We optimize actually not for top price. We optimize for you know, getting the business transition out quickly. We had already started workshop, our new company and we had some commitments there and that sort of thing.”
Derek Homann Nov 16, 2021 ▶ 7:59
Disclosure
Gazdecki: Prioritized favorable deal terms over a larger earnout at Bizness Apps
“I did that with business apps. I optimize for terms rather than like bigger and out and stuff like that.”
Andrew Gazdecki Nov 16, 2021 ▶ 9:09
Disclosure
Homann: Prior licensing deals inadvertently prepared the acquisition data room
“Those two perpetual licensing deals that we did before required us to do just a crap ton of due diligence. So we had this data room of all of our financials, all of our contracts and all that stuff, luckily already ready.”
Derek Homann Nov 16, 2021 ▶ 10:44
Assertion Not checkable as stated
Gazdecki: Startups connecting live analytics on MicroAcquire get 500% more requests
“We have data around startups that connect Stripe, or Barometrics, or any sort of analytics within MicroQuare. They get, like, 500% more buyer requests, because it really cuts down on the due diligence of the buyer.”
Andrew Gazdecki Nov 16, 2021 ▶ 14:57
Disclosure
Homann: Median's acquisition and perpetual licensing deals totaled nearly $2 million
“With the sale of median both with that and then the licensing deals that we did kind of all combined that ended up being close to two million bucks. The perpetual licensing deals were actually bigger than the acquisition price”
Derek Homann Nov 16, 2021 ▶ 15:53
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