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Jun 14, 2024 · 25m · startup-acquisition-stories

Startup Acquisition Stories With Bryan Digiorgio, Founder of 1840 & Company

Bryan DiGiorgio · 17m spoken Andrew Gazdecki · 4m spoken
0:00 / 0:00

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In this episode of Startup Acquisition Stories, host Andrew Gazdecki interviews Bryan DiGiorgio, founder of 1840 & Company, who shares insights on acquiring Paisy and Swearit via Acquire.com. DiGiorgio discusses the tactical complexities of cross-border due diligence, leveraging global remote teams for operational synergy, and practical exit advice for startup founders.

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 18% of the talking time here. How this is scored →

Andrew as informed peer 3.3 Guest teaching 3.1 Guest disagreement 0.1 Andrew pushing back 0.0
05100:0010:0020:000:24–4:20 · Andrew as informed peer 2/10 Bryan DiGiorgio's Entrepreneurial Journey and 1840 & Company Andrew conducts a welcoming interview open, asking straightforward background questions. Bryan details his career journey from corporate outsourcing to launching ventures and acquiring startups like Paisy.4:20–8:05 · Andrew as informed peer 2/10 Strategic Synergies Across Blockchain and Student Ventures Andrew prompts Bryan on his acquisition strategy and the Swearit deal. Bryan explains blockchain synergies and the operational hurdles of due diligence with a Spanish company.8:06–10:10 · Andrew as informed peer 4/10 Overcoming Cross-Border Roadblocks with M&A Advisory Andrew highlights Acquire's M&A advisory capabilities on both the buy and sell sides. Bryan praises the team for bridging cross-border and language barriers.10:11–13:24 · Andrew as informed peer 2/10 Navigating Legal Hurdles and Localization in Spain Bryan walks Andrew through the intricate legal realities of buying a Spanish company, detailing apostille requirements, translation bottlenecks, and choosing a stock deal.13:25–15:40 · Andrew as informed peer 2/10 Arbitrage Opportunities in Cross-Border Startup Acquisitions Andrew asks if Bryan would pursue European deals again. Bryan explains cross-border geographic arbitrage—bolting offshore assets onto US distribution to boost margins.15:40–20:11 · Andrew as informed peer 6/10 Market Insights and Overcoming Founder Valuation Disconnects Bryan critiques unrealistic founder valuation expectations on the marketplace. Andrew demonstrates marketplace expertise by explaining founder psychology and citing platform data on why overpriced listings fail to sell.20:12–23:58 · Andrew as informed peer 5/10 Essential M&A Advice for Exiting Startup Founders Bryan provides tactical tips for sellers, highlighting post-acquisition knowledge transfer and rollover equity incentives. Andrew reinforces the advice with practical transition examples.0:24–4:20 · Guest teaching 2/10 Bryan DiGiorgio's Entrepreneurial Journey and 1840 & Company Andrew conducts a welcoming interview open, asking straightforward background questions. Bryan details his career journey from corporate outsourcing to launching ventures and acquiring startups like Paisy.4:20–8:05 · Guest teaching 3/10 Strategic Synergies Across Blockchain and Student Ventures Andrew prompts Bryan on his acquisition strategy and the Swearit deal. Bryan explains blockchain synergies and the operational hurdles of due diligence with a Spanish company.8:06–10:10 · Guest teaching 1/10 Overcoming Cross-Border Roadblocks with M&A Advisory Andrew highlights Acquire's M&A advisory capabilities on both the buy and sell sides. Bryan praises the team for bridging cross-border and language barriers.10:11–13:24 · Guest teaching 5/10 Navigating Legal Hurdles and Localization in Spain Bryan walks Andrew through the intricate legal realities of buying a Spanish company, detailing apostille requirements, translation bottlenecks, and choosing a stock deal.13:25–15:40 · Guest teaching 4/10 Arbitrage Opportunities in Cross-Border Startup Acquisitions Andrew asks if Bryan would pursue European deals again. Bryan explains cross-border geographic arbitrage—bolting offshore assets onto US distribution to boost margins.15:40–20:11 · Guest teaching 3/10 Market Insights and Overcoming Founder Valuation Disconnects Bryan critiques unrealistic founder valuation expectations on the marketplace. Andrew demonstrates marketplace expertise by explaining founder psychology and citing platform data on why overpriced listings fail to sell.20:12–23:58 · Guest teaching 4/10 Essential M&A Advice for Exiting Startup Founders Bryan provides tactical tips for sellers, highlighting post-acquisition knowledge transfer and rollover equity incentives. Andrew reinforces the advice with practical transition examples.0:24–4:20 · Guest disagreement 0/10 Bryan DiGiorgio's Entrepreneurial Journey and 1840 & Company Andrew conducts a welcoming interview open, asking straightforward background questions. Bryan details his career journey from corporate outsourcing to launching ventures and acquiring startups like Paisy.4:20–8:05 · Guest disagreement 0/10 Strategic Synergies Across Blockchain and Student Ventures Andrew prompts Bryan on his acquisition strategy and the Swearit deal. Bryan explains blockchain synergies and the operational hurdles of due diligence with a Spanish company.8:06–10:10 · Guest disagreement 0/10 Overcoming Cross-Border Roadblocks with M&A Advisory Andrew highlights Acquire's M&A advisory capabilities on both the buy and sell sides. Bryan praises the team for bridging cross-border and language barriers.10:11–13:24 · Guest disagreement 0/10 Navigating Legal Hurdles and Localization in Spain Bryan walks Andrew through the intricate legal realities of buying a Spanish company, detailing apostille requirements, translation bottlenecks, and choosing a stock deal.13:25–15:40 · Guest disagreement 0/10 Arbitrage Opportunities in Cross-Border Startup Acquisitions Andrew asks if Bryan would pursue European deals again. Bryan explains cross-border geographic arbitrage—bolting offshore assets onto US distribution to boost margins.15:40–20:11 · Guest disagreement 1/10 Market Insights and Overcoming Founder Valuation Disconnects Bryan critiques unrealistic founder valuation expectations on the marketplace. Andrew demonstrates marketplace expertise by explaining founder psychology and citing platform data on why overpriced listings fail to sell.20:12–23:58 · Guest disagreement 0/10 Essential M&A Advice for Exiting Startup Founders Bryan provides tactical tips for sellers, highlighting post-acquisition knowledge transfer and rollover equity incentives. Andrew reinforces the advice with practical transition examples.0:24–4:20 · Andrew pushing back 0/10 Bryan DiGiorgio's Entrepreneurial Journey and 1840 & Company Andrew conducts a welcoming interview open, asking straightforward background questions. Bryan details his career journey from corporate outsourcing to launching ventures and acquiring startups like Paisy.4:20–8:05 · Andrew pushing back 0/10 Strategic Synergies Across Blockchain and Student Ventures Andrew prompts Bryan on his acquisition strategy and the Swearit deal. Bryan explains blockchain synergies and the operational hurdles of due diligence with a Spanish company.8:06–10:10 · Andrew pushing back 0/10 Overcoming Cross-Border Roadblocks with M&A Advisory Andrew highlights Acquire's M&A advisory capabilities on both the buy and sell sides. Bryan praises the team for bridging cross-border and language barriers.10:11–13:24 · Andrew pushing back 0/10 Navigating Legal Hurdles and Localization in Spain Bryan walks Andrew through the intricate legal realities of buying a Spanish company, detailing apostille requirements, translation bottlenecks, and choosing a stock deal.13:25–15:40 · Andrew pushing back 0/10 Arbitrage Opportunities in Cross-Border Startup Acquisitions Andrew asks if Bryan would pursue European deals again. Bryan explains cross-border geographic arbitrage—bolting offshore assets onto US distribution to boost margins.15:40–20:11 · Andrew pushing back 0/10 Market Insights and Overcoming Founder Valuation Disconnects Bryan critiques unrealistic founder valuation expectations on the marketplace. Andrew demonstrates marketplace expertise by explaining founder psychology and citing platform data on why overpriced listings fail to sell.20:12–23:58 · Andrew pushing back 0/10 Essential M&A Advice for Exiting Startup Founders Bryan provides tactical tips for sellers, highlighting post-acquisition knowledge transfer and rollover equity incentives. Andrew reinforces the advice with practical transition examples.

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

0:00 · Andrew 11.8% · guest 88.2%0:00 · Andrew 11.8% · guest 88.2%3:00 · Andrew 18.4% · guest 81.6%3:00 · Andrew 18.4% · guest 81.6%6:00 · Andrew 8.6% · guest 91.4%6:00 · Andrew 8.6% · guest 91.4%9:00 · Andrew 22.2% · guest 77.8%9:00 · Andrew 22.2% · guest 77.8%12:00 · Andrew 8.7% · guest 91.3%12:00 · Andrew 8.7% · guest 91.3%15:00 · Andrew 12.2% · guest 87.8%15:00 · Andrew 12.2% · guest 87.8%18:00 · Andrew 44.2% · guest 55.8%18:00 · Andrew 44.2% · guest 55.8%21:00 · Andrew 16.4% · guest 83.6%21:00 · Andrew 16.4% · guest 83.6%24:00 · Andrew 21.6% · guest 78.4%24:00 · Andrew 21.6% · guest 78.4%
Sharpest disagreement ▶ 17:25 Bryan points out wild valuation disconnects

Bryan critiques startup founders who unrealistically value 2 million dollar assets at 12 million dollars without proper SaaS metrics.

 Hardest push from Andrew ▶ 16:57 Andrew asks for blunt platform criticism

Andrew actively pushes Bryan to give honest, constructive criticism regarding what Acquire needs to improve on its platform.

 Biggest teaching moment ▶ 10:11 Bryan breaks down cross-border legal compliance

Bryan educates Andrew on the rigid, sequential legal hurdles of Spanish acquisitions, contrasting basic US notarization with costly apostilles and power of attorney translations.

 Andrew holds their own ▶ 18:15 Andrew explains SaaS valuation traps and marketplace dynamics

Andrew demonstrates domain expertise by sharing his own past founder misconceptions around 10x ARR multiples and confirming platform data on seller pricing errors.
the scores for every segment, with the reasoning behind each
ChapterTopicAndrew as informed peerGuest teachingGuest disagreementAndrew pushing backWhy
Bryan DiGiorgio's Entrepreneurial Journey and 1840 & Company 2200 Andrew conducts a welcoming interview open, asking straightforward background questions. Bryan details his career journey from corporate outsourcing to launching ventures and acquiring startups like Paisy.
Strategic Synergies Across Blockchain and Student Ventures 2300 Andrew prompts Bryan on his acquisition strategy and the Swearit deal. Bryan explains blockchain synergies and the operational hurdles of due diligence with a Spanish company.
Overcoming Cross-Border Roadblocks with M&A Advisory 4100 Andrew highlights Acquire's M&A advisory capabilities on both the buy and sell sides. Bryan praises the team for bridging cross-border and language barriers.
Navigating Legal Hurdles and Localization in Spain 2500 Bryan walks Andrew through the intricate legal realities of buying a Spanish company, detailing apostille requirements, translation bottlenecks, and choosing a stock deal.
Arbitrage Opportunities in Cross-Border Startup Acquisitions 2400 Andrew asks if Bryan would pursue European deals again. Bryan explains cross-border geographic arbitrage—bolting offshore assets onto US distribution to boost margins.
Market Insights and Overcoming Founder Valuation Disconnects 6310 Bryan critiques unrealistic founder valuation expectations on the marketplace. Andrew demonstrates marketplace expertise by explaining founder psychology and citing platform data on why overpriced listings fail to sell.
Essential M&A Advice for Exiting Startup Founders 5400 Bryan provides tactical tips for sellers, highlighting post-acquisition knowledge transfer and rollover equity incentives. Andrew reinforces the advice with practical transition examples.

Statements from this episode (9)

Disclosure
DiGiorgio: Building a Blockchain-Based Private Debt Marketplace
“You know, we're one of the other companies that we're actually building is a private debt marketplace. And that private that marketplace is going to be built within blockchain.”
Bryan DiGiorgio Jun 14, 2024 ▶ 4:33
Disclosure
DiGiorgio: 1840 Ventures Shifted Focus to Student Startups via Campus Roots
“We also have taken actually 1840 ventures and while. It was fairly generic as a venture studio and as we were thinking about it, we since morphed it to really target college students. In helping college students start companies and really trying to leverage th…”
Bryan DiGiorgio Jun 14, 2024 ▶ 5:10
Disclosure
1840 & Company Reached an LOI for Swearit Within 30 to 45 Days
“We went fairly quick, I think, through the initial process to get to a letter of intent with them. What the same might have been, 30 days could have been 45, but relatively short order.”
Bryan DiGiorgio Jun 14, 2024 ▶ 6:29
What-if
DiGiorgio: Delaying Cross-Border Legal Work Cost Us a Month in M&A
“If I understood it better, I would have started the process as we started due diligence. And not have lost that month in the due diligence to then start the process.”
Bryan DiGiorgio Jun 14, 2024 ▶ 11:29
Disclosure
DiGiorgio Used a Stock Purchase to Avoid Creating a Spanish Entity
“We decided to actually do an equity deal. With them and actually purchase stock. So it wasn't an asset. So, because I didn't want to go through trying to figure out how to set up a company in Spain.”
Bryan DiGiorgio Jun 14, 2024 ▶ 11:57
Assertion Not checkable as stated
DiGiorgio: Swearit Sells Across the EU Driven by Wine Labeling Rules
“Most, most of what's where it's doing right now is actually in the EU because of some legislation around wine labeling in the EU. So, we're effectively selling into all the countries into the EU with it.”
Bryan DiGiorgio Jun 14, 2024 ▶ 12:46
Insight
DiGiorgio: Foreign Operators Need Trusted Local Partners to Avoid Being Exploited
“You always need to get a person that's there that you trust. Locally, and, you know, that's just from experience from talking with. I'll say other foreigners that have companies that are in other countries, because as you being a foreigner. You know, people wi…”
Bryan DiGiorgio Jun 14, 2024 ▶ 14:38
Assertion Not checkable as stated
Gazdecki: Overpricing Is the Number One Reason Startups Fail to Sell
“And fun fact, that's actually the number one reason companies or startups on sale and acquires, they price too high. And what happens is a lot of buyers won't even talk to them or look at their business in the first place. They'll just go on to a business that…”
Andrew Gazdecki Jun 14, 2024 ▶ 19:52
Disclosure
DiGiorgio: 1840 Leaves Rollover Equity in Acquisitions to Retain Founder Support
“What we've done with some of our deal, with our two deals is actually we've left them with a piece of the equity. So, we require most. But, you know, we hopefully are giving them a taste at the end. So we, so they would help us more. With the transition and be…”
Bryan DiGiorgio Jun 14, 2024 ▶ 21:54
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