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Mar 4, 2025 · 37m · the-pitch

#119 Amateur Golf Society: Venture Capital vs. Private Equity

Dan Hershberg · 13m spoken Josh Muccio · 6m spoken Howie Diamond · 5m spoken Al Bsharah · 3m spoken Jillian Manus · 1m spoken Beck Bamberger · 1m spoken
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Entrepreneur Dan Hershberg pitches the Amateur Golf Society on The Pitch, securing tentative investor commitments that ultimately collapse over private equity board control. Despite venture capitalists withdrawing their offers over governance concerns, Dan successfully completes his funding round with studio angel investors and existing backers.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Josh holds 23.4% of the talking time here. How this is scored →

Josh as informed peer 6.4 Guest teaching 3.4 Guest disagreement 1.8 Josh pushing back 5.4
05100:0010:0020:0030:002:03–8:24 · Josh as informed peer 5/10 Dan Hershberg Pitches the Amateur Golf Society Dan pitches the Amateur Golf Society's flexible tournament model. The investors ask clarifying questions on operational mechanics, course economics, and tech integrations without much friction.8:25–13:53 · Josh as informed peer 6/10 Company Origin, Revenue Traction, and Concerning Equity Structure Dan details the company's origin out of a brewery and reveals that private equity owns 35% while he only retains 20%. The investors immediately flag this low founder equity as a major risk for future funding.13:54–20:58 · Josh as informed peer 6/10 Scaling Ambitions, Exit Strategy, and Investment Commitments Dan maps out his $30M cash-flow scaling target and exit aspirations. Despite Bec bowing out over operational complexity, Howie, Al, and Jillian are charmed by Dan's sales capability and verbally commit $250k.20:59–23:35 · Josh as informed peer 7/10 Governance Red Flags and Post-Pitch Investor Debrief Howie catches a crucial governance red flag: private equity controls 3 of the 5 board seats. The investors press Dan on his lack of voting control and discuss the issue among themselves after he departs.23:41–30:45 · Josh as informed peer 8/10 Boardroom Impasse and VC Withdrawal from the Deal After PE refuses to give up a board seat, the VCs formally pull their investment offers on a debrief call with Dan. They advise Dan on negotiation leverage and explain why the existing structure is predatory.2:03–8:24 · Guest teaching 4/10 Dan Hershberg Pitches the Amateur Golf Society Dan pitches the Amateur Golf Society's flexible tournament model. The investors ask clarifying questions on operational mechanics, course economics, and tech integrations without much friction.8:25–13:53 · Guest teaching 3/10 Company Origin, Revenue Traction, and Concerning Equity Structure Dan details the company's origin out of a brewery and reveals that private equity owns 35% while he only retains 20%. The investors immediately flag this low founder equity as a major risk for future funding.13:54–20:58 · Guest teaching 3/10 Scaling Ambitions, Exit Strategy, and Investment Commitments Dan maps out his $30M cash-flow scaling target and exit aspirations. Despite Bec bowing out over operational complexity, Howie, Al, and Jillian are charmed by Dan's sales capability and verbally commit $250k.20:59–23:35 · Guest teaching 2/10 Governance Red Flags and Post-Pitch Investor Debrief Howie catches a crucial governance red flag: private equity controls 3 of the 5 board seats. The investors press Dan on his lack of voting control and discuss the issue among themselves after he departs.23:41–30:45 · Guest teaching 5/10 Boardroom Impasse and VC Withdrawal from the Deal After PE refuses to give up a board seat, the VCs formally pull their investment offers on a debrief call with Dan. They advise Dan on negotiation leverage and explain why the existing structure is predatory.2:03–8:24 · Guest disagreement 1/10 Dan Hershberg Pitches the Amateur Golf Society Dan pitches the Amateur Golf Society's flexible tournament model. The investors ask clarifying questions on operational mechanics, course economics, and tech integrations without much friction.8:25–13:53 · Guest disagreement 2/10 Company Origin, Revenue Traction, and Concerning Equity Structure Dan details the company's origin out of a brewery and reveals that private equity owns 35% while he only retains 20%. The investors immediately flag this low founder equity as a major risk for future funding.13:54–20:58 · Guest disagreement 2/10 Scaling Ambitions, Exit Strategy, and Investment Commitments Dan maps out his $30M cash-flow scaling target and exit aspirations. Despite Bec bowing out over operational complexity, Howie, Al, and Jillian are charmed by Dan's sales capability and verbally commit $250k.20:59–23:35 · Guest disagreement 2/10 Governance Red Flags and Post-Pitch Investor Debrief Howie catches a crucial governance red flag: private equity controls 3 of the 5 board seats. The investors press Dan on his lack of voting control and discuss the issue among themselves after he departs.23:41–30:45 · Guest disagreement 2/10 Boardroom Impasse and VC Withdrawal from the Deal After PE refuses to give up a board seat, the VCs formally pull their investment offers on a debrief call with Dan. They advise Dan on negotiation leverage and explain why the existing structure is predatory.2:03–8:24 · Josh pushing back 2/10 Dan Hershberg Pitches the Amateur Golf Society Dan pitches the Amateur Golf Society's flexible tournament model. The investors ask clarifying questions on operational mechanics, course economics, and tech integrations without much friction.8:25–13:53 · Josh pushing back 6/10 Company Origin, Revenue Traction, and Concerning Equity Structure Dan details the company's origin out of a brewery and reveals that private equity owns 35% while he only retains 20%. The investors immediately flag this low founder equity as a major risk for future funding.13:54–20:58 · Josh pushing back 4/10 Scaling Ambitions, Exit Strategy, and Investment Commitments Dan maps out his $30M cash-flow scaling target and exit aspirations. Despite Bec bowing out over operational complexity, Howie, Al, and Jillian are charmed by Dan's sales capability and verbally commit $250k.20:59–23:35 · Josh pushing back 7/10 Governance Red Flags and Post-Pitch Investor Debrief Howie catches a crucial governance red flag: private equity controls 3 of the 5 board seats. The investors press Dan on his lack of voting control and discuss the issue among themselves after he departs.23:41–30:45 · Josh pushing back 8/10 Boardroom Impasse and VC Withdrawal from the Deal After PE refuses to give up a board seat, the VCs formally pull their investment offers on a debrief call with Dan. They advise Dan on negotiation leverage and explain why the existing structure is predatory.

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

0:00 · Josh 58.5% · guest 41.5%0:00 · Josh 58.5% · guest 41.5%3:00 · Josh 0% · guest 100%3:00 · Josh 0% · guest 100%6:00 · Josh 0% · guest 100%6:00 · Josh 0% · guest 100%9:00 · Josh 0% · guest 100%9:00 · Josh 0% · guest 100%12:00 · Josh 14.8% · guest 85.2%12:00 · Josh 14.8% · guest 85.2%15:00 · Josh 0% · guest 100%15:00 · Josh 0% · guest 100%18:00 · Josh 0% · guest 100%18:00 · Josh 0% · guest 100%21:00 · Josh 11.3% · guest 88.7%21:00 · Josh 11.3% · guest 88.7%24:00 · Josh 55.3% · guest 44.7%24:00 · Josh 55.3% · guest 44.7%27:00 · Josh 1.8% · guest 98.2%27:00 · Josh 1.8% · guest 98.2%30:00 · Josh 35.9% · guest 64.1%30:00 · Josh 35.9% · guest 64.1%33:00 · Josh 64.3% · guest 35.7%33:00 · Josh 64.3% · guest 35.7%36:00 · Josh 100% · guest 0%36:00 · Josh 100% · guest 0%
Sharpest disagreement ▶ 28:59 Dan pushes back on the assumption he had alternatives

Dan defends his past actions to the VCs, arguing he had no alternative when carving assets out of the brewery because he did not own the IP.

 Hardest push from Josh ▶ 27:28 Howie calls the equity split and board control egregious

Howie refuses to participate in the deal, directly criticizing the PE partners for protecting their own downside rather than empowering the founder.

 Biggest teaching moment ▶ 29:45 Al and Jillian educate Dan on founder leverage

Al and Jillian explain to Dan that because he is the sole driving force behind the company, he had immense leverage to demand majority equity and control.

 Josh holds their own ▶ 21:08 Investors highlight the risk of PE firing Dan at will

Howie and Jillian demonstrate their institutional governance knowledge by calling out that Dan can be voted out of his own company tomorrow under his current board structure.
the scores for every segment, with the reasoning behind each
ChapterTopicJosh as informed peerGuest teachingGuest disagreementJosh pushing backWhy
Dan Hershberg Pitches the Amateur Golf Society 5412 Dan pitches the Amateur Golf Society's flexible tournament model. The investors ask clarifying questions on operational mechanics, course economics, and tech integrations without much friction.
Company Origin, Revenue Traction, and Concerning Equity Structure 6326 Dan details the company's origin out of a brewery and reveals that private equity owns 35% while he only retains 20%. The investors immediately flag this low founder equity as a major risk for future funding.
Scaling Ambitions, Exit Strategy, and Investment Commitments 6324 Dan maps out his $30M cash-flow scaling target and exit aspirations. Despite Bec bowing out over operational complexity, Howie, Al, and Jillian are charmed by Dan's sales capability and verbally commit $250k.
Governance Red Flags and Post-Pitch Investor Debrief 7227 Howie catches a crucial governance red flag: private equity controls 3 of the 5 board seats. The investors press Dan on his lack of voting control and discuss the issue among themselves after he departs.
Boardroom Impasse and VC Withdrawal from the Deal 8528 After PE refuses to give up a board seat, the VCs formally pull their investment offers on a debrief call with Dan. They advise Dan on negotiation leverage and explain why the existing structure is predatory.

Statements from this episode (11)

Assertion Not checkable as stated
Hershberg: Amateur Golf Society doubled membership and tripled engagement in pilot
“After two years of proof of concept, we saw membership double and we saw engagement nearly triple.”
Dan Hershberg Mar 4, 2025 ▶ 3:04
Assertion Supported
Hershberg: Golf participation is up nearly 20% from pre-pandemic levels
“So the growth in the game is nearly 20% from what it was prior to the pandemic.”
Dan Hershberg Mar 4, 2025 ▶ 3:30
Assertion Not checkable as stated
Hershberg: Amateur Golf Society closes roughly 85% of pitched courses
“Close rate is about 85% of the courses that I talk to.”
Dan Hershberg Mar 4, 2025 ▶ 6:37
Prediction Not checkable as stated
Hershberg: Amateur Golf Society will generate around $200k in revenue this year
“So total revenue this year is probably going to be somewhere around 200,000 dollars would be my guess.”
Dan Hershberg Mar 4, 2025 ▶ 10:04
Disclosure
Hershberg: PE backer gained stake by forgiving $2M in brewery debt
“What they did, so they basically forgave two million dollars worth of debt that was owed to the to them from the brewery to set the valuation. And then that's how we kind of got things started. So they didn't put any new money into it for this particular round…”
Dan Hershberg Mar 4, 2025 ▶ 11:43
Assertion Not checkable as stated
Hershberg: 2,500 members in 58 markets would yield $30M annual cash flow
“So if we look at every single AGA in the country, of which there are 58, if each one of those markets has an AGS tour in it with 2500 members. This business is cash flowing thirty million dollars a year.”
Dan Hershberg Mar 4, 2025 ▶ 14:31
Assertion Not checkable as stated
Hershberg: Private equity controls three of Amateur Golf Society's five board seats
“So there's five board seats. There's three for the private equity guys, one for myself and one for the group of fellow Cornellians.”
Dan Hershberg Mar 4, 2025 ▶ 21:24
Assertion Not checkable as stated
Bsharah: PE offered VCs an observer seat and 18-month CEO retention guarantee
“They essentially said, They would give us a board observer seat and promise not to fire the CEO for 18 months.”
Al Bsharah Mar 4, 2025 ▶ 25:37
Opinion
Diamond: Hershberg's 20% equity versus PE's 80% is egregious
“You only own 20% of the company. Meanwhile, the original partners of the brewery own 80% of the company. It's our opinion that, like, fundamentally those numbers are a bit egregious, and we think, like, they literally should be swapped.”
Howie Diamond Mar 4, 2025 ▶ 27:29
Assertion Not checkable as stated
Muccio: Two studio angel investors put $25k into Amateur Golf Society
“There were these two investors in the studio with us that day, angel investors in our media company, actually. They invested 25,000 in AGS.”
Josh Muccio Mar 4, 2025 ▶ 32:41
Assertion Not publicly verifiable
Muccio: Hershberg closed $1M round for AGS with existing investors
“FYI, Dan closed out the rest of his one million dollar round from his existing investors.”
Josh Muccio Mar 4, 2025 ▶ 33:15
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