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Mar 3, 2025 · 30m · the-pitch

#68 Dogs & Dating: A Match Made in Heaven?

Leigh Isaacson · 12m spoken Josh Muccio · 5m spoken Soraya Daraby · 1m spoken Michael Hyatt · 1m spoken Charles Hudson · 1m spoken Sarah Downey · 1m spoken Heather Rogers · 55s spoken Phil Nadel · 49s spoken
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Founder Leigh Isaacson pitches Dig, a dating application for dog lovers, to a panel of venture capitalists on The Pitch. Despite intense debate over venture scale and valuation, Leigh secures an investment from Charles Hudson and subsequently recalibrates her fundraising strategy to gain strong deal momentum.

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 23.9% of the talking time here. How this is scored →

Josh as informed peer 1.6 Guest teaching 2.8 Guest disagreement 1.6 Josh pushing back 4.2
05100:0010:0020:0030:001:50–6:48 · Josh as informed peer 1/10 The Origin Story and Penny the Dog Leigh opens with a polished pitch and charming presentation of her dog Penny, quickly handling Michael Hyatt's questions about user acquisition and defensibility with clear statistics on dating app behavior and CAC.6:48–9:25 · Josh as informed peer 1/10 Revenue Streams and the Early Acquisition Temptation Investors probe Dig's revenue model and path to scale; Leigh surprises the panel by admitting she would readily take an early acquisition offer from a dating conglomerate like Badoo.9:45–12:44 · Josh as informed peer 1/10 Market Scope: Expanding Beyond Dogs vs. Strategic Focus Soraya presses Leigh to choose between pursuing a massive verticalized network or selling early for 50 million, while Leigh resists narrowing her options and argues for keeping all doors open.12:45–20:03 · Josh as informed peer 1/10 Valuation Scrutiny and Investor Deliberation Charles offers a small 10k check while Phil, Michael, and Soraya pass due to the 4.5 million valuation and lack of a focused, massive vision.20:08–29:10 · Josh as informed peer 4/10 Post-Pitch Investor Debrief with Charles Hudson Josh presses Charles on why his check size was unusually small, followed by Heather Rogers debriefing Leigh on cutting her valuation immediately after the pitch.1:50–6:48 · Guest teaching 4/10 The Origin Story and Penny the Dog Leigh opens with a polished pitch and charming presentation of her dog Penny, quickly handling Michael Hyatt's questions about user acquisition and defensibility with clear statistics on dating app behavior and CAC.6:48–9:25 · Guest teaching 3/10 Revenue Streams and the Early Acquisition Temptation Investors probe Dig's revenue model and path to scale; Leigh surprises the panel by admitting she would readily take an early acquisition offer from a dating conglomerate like Badoo.9:45–12:44 · Guest teaching 3/10 Market Scope: Expanding Beyond Dogs vs. Strategic Focus Soraya presses Leigh to choose between pursuing a massive verticalized network or selling early for 50 million, while Leigh resists narrowing her options and argues for keeping all doors open.12:45–20:03 · Guest teaching 2/10 Valuation Scrutiny and Investor Deliberation Charles offers a small 10k check while Phil, Michael, and Soraya pass due to the 4.5 million valuation and lack of a focused, massive vision.20:08–29:10 · Guest teaching 2/10 Post-Pitch Investor Debrief with Charles Hudson Josh presses Charles on why his check size was unusually small, followed by Heather Rogers debriefing Leigh on cutting her valuation immediately after the pitch.1:50–6:48 · Guest disagreement 1/10 The Origin Story and Penny the Dog Leigh opens with a polished pitch and charming presentation of her dog Penny, quickly handling Michael Hyatt's questions about user acquisition and defensibility with clear statistics on dating app behavior and CAC.6:48–9:25 · Guest disagreement 2/10 Revenue Streams and the Early Acquisition Temptation Investors probe Dig's revenue model and path to scale; Leigh surprises the panel by admitting she would readily take an early acquisition offer from a dating conglomerate like Badoo.9:45–12:44 · Guest disagreement 2/10 Market Scope: Expanding Beyond Dogs vs. Strategic Focus Soraya presses Leigh to choose between pursuing a massive verticalized network or selling early for 50 million, while Leigh resists narrowing her options and argues for keeping all doors open.12:45–20:03 · Guest disagreement 1/10 Valuation Scrutiny and Investor Deliberation Charles offers a small 10k check while Phil, Michael, and Soraya pass due to the 4.5 million valuation and lack of a focused, massive vision.20:08–29:10 · Guest disagreement 2/10 Post-Pitch Investor Debrief with Charles Hudson Josh presses Charles on why his check size was unusually small, followed by Heather Rogers debriefing Leigh on cutting her valuation immediately after the pitch.1:50–6:48 · Josh pushing back 2/10 The Origin Story and Penny the Dog Leigh opens with a polished pitch and charming presentation of her dog Penny, quickly handling Michael Hyatt's questions about user acquisition and defensibility with clear statistics on dating app behavior and CAC.6:48–9:25 · Josh pushing back 4/10 Revenue Streams and the Early Acquisition Temptation Investors probe Dig's revenue model and path to scale; Leigh surprises the panel by admitting she would readily take an early acquisition offer from a dating conglomerate like Badoo.9:45–12:44 · Josh pushing back 5/10 Market Scope: Expanding Beyond Dogs vs. Strategic Focus Soraya presses Leigh to choose between pursuing a massive verticalized network or selling early for 50 million, while Leigh resists narrowing her options and argues for keeping all doors open.12:45–20:03 · Josh pushing back 6/10 Valuation Scrutiny and Investor Deliberation Charles offers a small 10k check while Phil, Michael, and Soraya pass due to the 4.5 million valuation and lack of a focused, massive vision.20:08–29:10 · Josh pushing back 4/10 Post-Pitch Investor Debrief with Charles Hudson Josh presses Charles on why his check size was unusually small, followed by Heather Rogers debriefing Leigh on cutting her valuation immediately after the pitch.

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

0:00 · Josh 56.6% · guest 43.4%0:00 · Josh 56.6% · guest 43.4%3:00 · Josh 5% · guest 95%3:00 · Josh 5% · guest 95%6:00 · Josh 3.4% · guest 96.6%6:00 · Josh 3.4% · guest 96.6%9:00 · Josh 34.4% · guest 65.6%9:00 · Josh 34.4% · guest 65.6%12:00 · Josh 9.7% · guest 90.3%12:00 · Josh 9.7% · guest 90.3%15:00 · Josh 5.1% · guest 94.9%15:00 · Josh 5.1% · guest 94.9%18:00 · Josh 6.8% · guest 93.2%18:00 · Josh 6.8% · guest 93.2%21:00 · Josh 27.4% · guest 72.6%21:00 · Josh 27.4% · guest 72.6%24:00 · Josh 21.8% · guest 78.2%24:00 · Josh 21.8% · guest 78.2%27:00 · Josh 50.2% · guest 49.8%27:00 · Josh 50.2% · guest 49.8%30:00 · Josh 100% · guest 0%30:00 · Josh 100% · guest 0%
Sharpest disagreement ▶ 12:00 Leigh rejects binary strategic path

When Soraya demands that Leigh choose between a fast exit and building a massive multi-vertical company, Leigh explicitly refuses the forced choice and defends building for all outcomes simultaneously.

 Hardest push from Josh ▶ 11:40 Soraya challenges Leigh's ambition and direction

Soraya directly confronts Leigh's lack of a definitive vision, pushing back on whether she wants to be an acquirable 50 million dollar business or take on the industry giants.

 Biggest teaching moment ▶ 5:39 Leigh educates Michael on dating app dynamics and CAC

Leigh counters assumptions about scaling costs by citing detailed blended CAC figures, specific Facebook ad channels, and high female user ratios.

 Josh holds their own ▶ 20:08 Josh probes Charles on his small investment

Josh immediately challenges Charles upon entering the room, demanding to know why a fund of Precursor's size wrote an unusually tiny 10k check.
the scores for every segment, with the reasoning behind each
ChapterTopicJosh as informed peerGuest teachingGuest disagreementJosh pushing backWhy
The Origin Story and Penny the Dog 1412 Leigh opens with a polished pitch and charming presentation of her dog Penny, quickly handling Michael Hyatt's questions about user acquisition and defensibility with clear statistics on dating app behavior and CAC.
Revenue Streams and the Early Acquisition Temptation 1324 Investors probe Dig's revenue model and path to scale; Leigh surprises the panel by admitting she would readily take an early acquisition offer from a dating conglomerate like Badoo.
Market Scope: Expanding Beyond Dogs vs. Strategic Focus 1325 Soraya presses Leigh to choose between pursuing a massive verticalized network or selling early for 50 million, while Leigh resists narrowing her options and argues for keeping all doors open.
Valuation Scrutiny and Investor Deliberation 1216 Charles offers a small 10k check while Phil, Michael, and Soraya pass due to the 4.5 million valuation and lack of a focused, massive vision.
Post-Pitch Investor Debrief with Charles Hudson 4224 Josh presses Charles on why his check size was unusually small, followed by Heather Rogers debriefing Leigh on cutting her valuation immediately after the pitch.

Statements from this episode (15)

Assertion Not checkable as stated
Isaacson: Dig reaches 80k downloads and 25k monthly active users
“In the past few months, we've seen 80,000 total downloads and 25,000 monthly active users looking for love on Dig.”
Leigh Isaacson Mar 3, 2025 ▶ 2:42
Disclosure
Isaacson: Dig is raising $1.5 million to scale
“We're raising 1.5 million dollars to scale and help people find someone they really dig.”
Leigh Isaacson Mar 3, 2025 ▶ 2:51
Assertion Partly supported
Isaacson: Dating app industry to reach $12B by end of next year
“In 2016, it was a three billion dollar industry. By the end of next year is expected to be a twelve billion dollar industry.”
Leigh Isaacson Mar 3, 2025 ▶ 4:55
Assertion Partly supported
Isaacson: Average user spends up to 10 hours weekly across 3-4 dating apps
“Your average dating app user uses three or four dating apps at a time for up to 10 hours a week on average.”
Leigh Isaacson Mar 3, 2025 ▶ 5:54
Disclosure
Isaacson: Dig achieves $1.40 blended CAC and $0.50 lowest CPI
“Our blended cost of user acquisition is a dollar 40 cents. Our lowest campaign is down to 50 cents cost per install.”
Leigh Isaacson Mar 3, 2025 ▶ 6:16
Disclosure
Isaacson: Dig's user base is approximately 70% women
“We have about 70% women on our dating app.”
Leigh Isaacson Mar 3, 2025 ▶ 6:31
Assertion Supported
Isaacson: 10% of dating app users select paid subscription tiers
“So dating apps today, according to industry data, you're seeing about 10% of users choosing to do one of the paid options between the two 99 and 34 dollars a month.”
Leigh Isaacson Mar 3, 2025 ▶ 7:34
Disclosure
Isaacson: Dig generated approximately $15,000 in total revenue this year
“So total this year has been about 15,000 dollars.”
Leigh Isaacson Mar 3, 2025 ▶ 8:08
Assertion Not checkable as stated
Isaacson: Badoo founder launched $100M initiative to acquire niche dating apps
“So for example, the billionaire founder of Badu reached out to us just two weeks ago. They're starting a one hundred million dollar initiative to find niche dating apps and bring them into the fold.”
Leigh Isaacson Mar 3, 2025 ▶ 8:47
Assertion Not checkable as stated
Isaacson: Dig has $350,000 soft-circled for seed round
“We have been pitching and we have about 350,000 dollars soft circled.”
Leigh Isaacson Mar 3, 2025 ▶ 14:41
Disclosure
Hudson commits $10,000 check to dating startup Dig
“So I'm in for 10,000.”
Charles Hudson Mar 3, 2025 ▶ 14:50
Prediction Not checkable as stated
Hyatt: Dig is likely to be acquired quickly at modest price
“I think it's likely that you're going to get acquired, and the number's not going to be that high, but it's going to change your life, and I think it's going to be a lot of money for you, but I'd rather have a better multiple, because I think you're going to g…”
Michael Hyatt Mar 3, 2025 ▶ 19:01
Disclosure
Hudson: Precursor Ventures typically writes $250,000 initial checks
“I just didn't feel like our normal full-size, two 50 K check was the right one in this case.”
Charles Hudson Mar 3, 2025 ▶ 20:21
Opinion
Hudson: Dig will not become a gigantic company
“I don't see this becoming a gigantic company.”
Charles Hudson Mar 3, 2025 ▶ 20:28
Assertion Not checkable as stated
Hudson: Every pet startup Precursor backed outperformed initial size expectations
“Everything we've done in pet has ended up being bigger than I thought going in.”
Charles Hudson Mar 3, 2025 ▶ 20:31
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