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May 13, 2016 · 27m · 20vc

20VC: Creating A Competitive Process Between VCs & Having Bill Gurley As A Board Member with Aaron Hirschhorn, Founder & CEO @ DogVacay

Aaron Hirschhorn · 18m spoken Harry Stebbings · 7m spoken
0:00 / 0:00

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In this episode of The 20 Minute VC, host Harry Stebbings interviews Aaron Hirschhorn, founder and CEO of DogVacay, to discuss building a $47 million venture-backed pet services marketplace. Aaron shares actionable strategies on overcoming early investor skepticism, running a competitive fundraising process, working with Benchmark's Bill Gurley, and establishing trust in high-stakes marketplace platforms.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 27.6% of the talking time here. How this is scored →

Harry as informed peer 3.2 Guest teaching 4.4 Guest disagreement 1.4 Harry pushing back 1.8
05100:0010:0020:002:04–5:12 · Harry as informed peer 2/10 DogVacay's Origin Story & Early Product-Market Fit Harry asks standard origin story questions to establish the narrative around DogVacay's founding. Aaron explains the marketplace dynamics, highlighting that demand acquisition is far harder than supply when dealing with pet care.5:12–7:58 · Harry as informed peer 3/10 Overcoming VC Skepticism & Pitching a Pet Business Harry pushes slightly by asking when the business stopped being seen as 'fluffy' and became a potential behemoth. Aaron gently reframes the 'behemoth' label and details how his own experience as a sitter helped overcome VC skepticism.7:58–13:35 · Harry as informed peer 4/10 Mastering the Fundraising Process & Creating VC Competition Harry interjects with ecosystem knowledge regarding Peter Pham's fund affiliation while guiding the fundraising discussion. Aaron delivers a detailed breakdown on running a tight, competitive venture capital process.13:35–19:27 · Harry as informed peer 4/10 On-Demand Economy Dynamics & Working with Bill Gurley Harry directs the discussion toward on-demand economy models and balancing growth with unit economics. Aaron offers a clear thesis separating cost-reducing services like UberX from overpriced convenience delivery apps.19:27–26:11 · Harry as informed peer 3/10 Building Trust in Marketplace Platforms Harry moves through trust mechanisms into a quick-fire round covering technical debt and success metrics. Aaron educates on why standard background checks are insufficient for trust-heavy platforms and reflects candidly on early tech debt.2:04–5:12 · Guest teaching 3/10 DogVacay's Origin Story & Early Product-Market Fit Harry asks standard origin story questions to establish the narrative around DogVacay's founding. Aaron explains the marketplace dynamics, highlighting that demand acquisition is far harder than supply when dealing with pet care.5:12–7:58 · Guest teaching 4/10 Overcoming VC Skepticism & Pitching a Pet Business Harry pushes slightly by asking when the business stopped being seen as 'fluffy' and became a potential behemoth. Aaron gently reframes the 'behemoth' label and details how his own experience as a sitter helped overcome VC skepticism.7:58–13:35 · Guest teaching 5/10 Mastering the Fundraising Process & Creating VC Competition Harry interjects with ecosystem knowledge regarding Peter Pham's fund affiliation while guiding the fundraising discussion. Aaron delivers a detailed breakdown on running a tight, competitive venture capital process.13:35–19:27 · Guest teaching 5/10 On-Demand Economy Dynamics & Working with Bill Gurley Harry directs the discussion toward on-demand economy models and balancing growth with unit economics. Aaron offers a clear thesis separating cost-reducing services like UberX from overpriced convenience delivery apps.19:27–26:11 · Guest teaching 5/10 Building Trust in Marketplace Platforms Harry moves through trust mechanisms into a quick-fire round covering technical debt and success metrics. Aaron educates on why standard background checks are insufficient for trust-heavy platforms and reflects candidly on early tech debt.2:04–5:12 · Guest disagreement 1/10 DogVacay's Origin Story & Early Product-Market Fit Harry asks standard origin story questions to establish the narrative around DogVacay's founding. Aaron explains the marketplace dynamics, highlighting that demand acquisition is far harder than supply when dealing with pet care.5:12–7:58 · Guest disagreement 2/10 Overcoming VC Skepticism & Pitching a Pet Business Harry pushes slightly by asking when the business stopped being seen as 'fluffy' and became a potential behemoth. Aaron gently reframes the 'behemoth' label and details how his own experience as a sitter helped overcome VC skepticism.7:58–13:35 · Guest disagreement 1/10 Mastering the Fundraising Process & Creating VC Competition Harry interjects with ecosystem knowledge regarding Peter Pham's fund affiliation while guiding the fundraising discussion. Aaron delivers a detailed breakdown on running a tight, competitive venture capital process.13:35–19:27 · Guest disagreement 2/10 On-Demand Economy Dynamics & Working with Bill Gurley Harry directs the discussion toward on-demand economy models and balancing growth with unit economics. Aaron offers a clear thesis separating cost-reducing services like UberX from overpriced convenience delivery apps.19:27–26:11 · Guest disagreement 1/10 Building Trust in Marketplace Platforms Harry moves through trust mechanisms into a quick-fire round covering technical debt and success metrics. Aaron educates on why standard background checks are insufficient for trust-heavy platforms and reflects candidly on early tech debt.2:04–5:12 · Harry pushing back 1/10 DogVacay's Origin Story & Early Product-Market Fit Harry asks standard origin story questions to establish the narrative around DogVacay's founding. Aaron explains the marketplace dynamics, highlighting that demand acquisition is far harder than supply when dealing with pet care.5:12–7:58 · Harry pushing back 3/10 Overcoming VC Skepticism & Pitching a Pet Business Harry pushes slightly by asking when the business stopped being seen as 'fluffy' and became a potential behemoth. Aaron gently reframes the 'behemoth' label and details how his own experience as a sitter helped overcome VC skepticism.7:58–13:35 · Harry pushing back 2/10 Mastering the Fundraising Process & Creating VC Competition Harry interjects with ecosystem knowledge regarding Peter Pham's fund affiliation while guiding the fundraising discussion. Aaron delivers a detailed breakdown on running a tight, competitive venture capital process.13:35–19:27 · Harry pushing back 2/10 On-Demand Economy Dynamics & Working with Bill Gurley Harry directs the discussion toward on-demand economy models and balancing growth with unit economics. Aaron offers a clear thesis separating cost-reducing services like UberX from overpriced convenience delivery apps.19:27–26:11 · Harry pushing back 1/10 Building Trust in Marketplace Platforms Harry moves through trust mechanisms into a quick-fire round covering technical debt and success metrics. Aaron educates on why standard background checks are insufficient for trust-heavy platforms and reflects candidly on early tech debt.

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

0:00 · Harry 72.8% · guest 27.2%0:00 · Harry 72.8% · guest 27.2%3:00 · Harry 25.9% · guest 74.1%3:00 · Harry 25.9% · guest 74.1%6:00 · Harry 14.7% · guest 85.3%6:00 · Harry 14.7% · guest 85.3%9:00 · Harry 16.1% · guest 83.9%9:00 · Harry 16.1% · guest 83.9%12:00 · Harry 16.1% · guest 83.9%12:00 · Harry 16.1% · guest 83.9%15:00 · Harry 18.9% · guest 81.1%15:00 · Harry 18.9% · guest 81.1%18:00 · Harry 9.7% · guest 90.3%18:00 · Harry 9.7% · guest 90.3%21:00 · Harry 23.4% · guest 76.6%21:00 · Harry 23.4% · guest 76.6%24:00 · Harry 33.6% · guest 66.4%24:00 · Harry 33.6% · guest 66.4%27:00 · Harry 100% · guest 0%27:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 14:45 Critiquing on-demand delivery unit economics

Aaron forcefully dismisses hype around undifferentiated food delivery platforms, arguing that heavy competition and poor unit economics will prevent most from surviving.

 Hardest push from Harry ▶ 5:12 Challenging the 'fluffy business' perception

Harry explicitly asks Aaron when DogVacay shifted from being a 'fluffy business' that VCs laughed at to a serious venture-backed company.

 Biggest teaching moment ▶ 10:55 Strategic batching of venture capital pitches

Aaron educates the audience and host on fundraise mechanics, advising founders to pitch lower-priority VCs during the first two weeks for practice before pitching tier-one targets in week three.

 Harry holds his own ▶ 8:28 Identifying Peter Pham's firm

Harry demonstrates his venture industry knowledge by instantly confirming that advisor Peter Pham is affiliated with Science when Aaron mentions his guidance.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
DogVacay's Origin Story & Early Product-Market Fit 2311 Harry asks standard origin story questions to establish the narrative around DogVacay's founding. Aaron explains the marketplace dynamics, highlighting that demand acquisition is far harder than supply when dealing with pet care.
Overcoming VC Skepticism & Pitching a Pet Business 3423 Harry pushes slightly by asking when the business stopped being seen as 'fluffy' and became a potential behemoth. Aaron gently reframes the 'behemoth' label and details how his own experience as a sitter helped overcome VC skepticism.
Mastering the Fundraising Process & Creating VC Competition 4512 Harry interjects with ecosystem knowledge regarding Peter Pham's fund affiliation while guiding the fundraising discussion. Aaron delivers a detailed breakdown on running a tight, competitive venture capital process.
On-Demand Economy Dynamics & Working with Bill Gurley 4522 Harry directs the discussion toward on-demand economy models and balancing growth with unit economics. Aaron offers a clear thesis separating cost-reducing services like UberX from overpriced convenience delivery apps.
Building Trust in Marketplace Platforms 3511 Harry moves through trust mechanisms into a quick-fire round covering technical debt and success metrics. Aaron educates on why standard background checks are insufficient for trust-heavy platforms and reflects candidly on early tech debt.

Statements from this episode (13)

Assertion Supported
US dog population stands at 83 million, outnumbering children
“There's eighty-three million dogs in the U.S., which is more than there are kids, by the way.”
Aaron Hirschhorn May 13, 2016 ▶ 2:54
Assertion Contradicted
US pet services is a fragmented $15B market with no dominant player
“The pet services market is fifteen billion dollars in the U.S. And completely fragmented, where nobody has even a couple points of market share, so it's a wide open opportunity.”
Aaron Hirschhorn May 13, 2016 ▶ 3:00
Disclosure
DogVacay approves only 15% of dog sitter applications
“We approve only about 15% of our dog sitter applications.”
Aaron Hirschhorn May 13, 2016 ▶ 3:40
Disclosure
DogVacay scaled to hundreds of thousands monthly within three months
“Three months in, we were doing a few 100,000 dollars a month.”
Aaron Hirschhorn May 13, 2016 ▶ 4:30
Assertion Not checkable as stated
Hirschhorn personally hosted over 100 dogs in 2011 as DogVacay's first host
“I had actually watched over a hundred dogs in my home over the course of 20 11 being the dog sitter, being the very first dog vacay sitter.”
Aaron Hirschhorn May 13, 2016 ▶ 5:51
Insight
Competition is the best lever to get hesitant VCs to invest
“There is nothing like competition to get people to write a check that they might otherwise be hesitant to write.”
Aaron Hirschhorn May 13, 2016 ▶ 9:07
Disclosure
DogVacay pitched 30 VC firms during its Series A raise
“For the series A, I probably did 30 pitches.”
Aaron Hirschhorn May 13, 2016 ▶ 11:30
Assertion Supported
DogVacay costs 40% less on average than traditional kennels
“And then, of course, selfishly, I'll put a dog vacay in that category, where we offer a far better experience than the kennel, and at about 40% less, on average, of cost.”
Aaron Hirschhorn May 13, 2016 ▶ 14:17
Prediction Held up
Hirschhorn predicts lack of differentiation will kill food delivery startups
“Food delivery space is a great example. Massive fucking market, don't get me wrong, like, massive market opportunity, but at the end of the day, there's not a lot of differentiation. All these guys are gonna be battling on price, and they're not all gonna surv…”
Aaron Hirschhorn May 13, 2016 ▶ 15:14
Assertion Partly supported
DogVacay leads the pet services market with under 1% penetration
“We're the leader in the space, but have a market share of, you know, 50 basis points, less than one percent.”
Aaron Hirschhorn May 13, 2016 ▶ 16:01
Opinion
Hirschhorn argues standard sharing economy background checks are highly imperfect
“They've become table stakes for the sharing economy. Between you and me, and I guess all of our listeners, I think they're far from sufficient to really tell you that background checks are highly imperfect. They only look at a certain time frame. They only loo…”
Aaron Hirschhorn May 13, 2016 ▶ 20:20
Insight
High-trust marketplace platforms must build proprietary vetting systems
“I think every business where trust is important needs to develop something of their own that's proprietary.”
Aaron Hirschhorn May 13, 2016 ▶ 20:37
Assertion Supported
DogVacay hosts nearly 30,000 active pet sitters on its platform
“Now we've got about 25,000, close to 30,000 sitters on our platform who are earning income, millions of dogs who are not in cages.”
Aaron Hirschhorn May 13, 2016 ▶ 24:15
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