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May 7, 2015 · 25m · 20vc

20 VC 034: 250 Investments, AngelList Syndicates and Microsoft with Jon Staenberg

Jon Staenberg · 15m spoken Harry Stebbings · 3m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this episode of The 20 Minute VC, host Harry Stebbings interviews veteran venture capitalist Jon Staenberg about his foundational years at Microsoft, his framework for evaluating startup pitches, and the impact of AngelList syndicates on modern funding.

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 29.6% of the talking time here. How this is scored →

Harry as informed peer 1.2 Guest teaching 1.7 Guest disagreement 0.5 Harry pushing back 0.0
05100:0010:0020:000:59–3:05 · Harry as informed peer 1/10 Early Career, Education, and Path to Venture Capital Harry asks a standard conversational opening question about Jon's background and entry into VC. Jon shares an extended backstory about Stanford, working in Taiwan, and receiving advice from Woody Howes to gain operational experience at Microsoft before entering venture capital.3:06–5:10 · Harry as informed peer 1/10 Key Lessons and Culture from Microsoft Harry asks straightforward open-ended questions regarding Jon's lessons from Microsoft and key leadership traits. Jon answers cooperatively with general insights on mission clarity and leadership vision.5:10–8:45 · Harry as informed peer 1/10 Investment Strategy, Pitch Criteria, and Kitchen Bowl Jon gently corrects Harry's premise regarding his track record, clarifying he has made over 250 investments rather than 100. He then discusses his opportunistic investment approach, including his recent deal in Kitchen Bowl.8:45–12:46 · Harry as informed peer 1/10 Evaluating Market Size and Emerging Technologies Jon reframes Harry's question on market sizing by noting that market forecast slides in pitches are largely made-up numbers. He later offers a candid assessment that VCs tend to overstate their value add to founders.12:46–18:14 · Harry as informed peer 2/10 Founder Due Diligence and the Impact of AngelList Syndicates Harry asks about due diligence and how AngelList syndicates affect traditional VC models. Jon details macro industry changes, including the consolidation of traditional funds and how platforms like AngelList provide deal-flow optionality.18:14–21:05 · Harry as informed peer 1/10 Inbound Pitch Management and Referral Channels Jon explains his high inbound volume and need for warm referrals, followed by a lighthearted and cooperative quick-fire lightning round.0:59–3:05 · Guest teaching 1/10 Early Career, Education, and Path to Venture Capital Harry asks a standard conversational opening question about Jon's background and entry into VC. Jon shares an extended backstory about Stanford, working in Taiwan, and receiving advice from Woody Howes to gain operational experience at Microsoft before entering venture capital.3:06–5:10 · Guest teaching 1/10 Key Lessons and Culture from Microsoft Harry asks straightforward open-ended questions regarding Jon's lessons from Microsoft and key leadership traits. Jon answers cooperatively with general insights on mission clarity and leadership vision.5:10–8:45 · Guest teaching 3/10 Investment Strategy, Pitch Criteria, and Kitchen Bowl Jon gently corrects Harry's premise regarding his track record, clarifying he has made over 250 investments rather than 100. He then discusses his opportunistic investment approach, including his recent deal in Kitchen Bowl.8:45–12:46 · Guest teaching 2/10 Evaluating Market Size and Emerging Technologies Jon reframes Harry's question on market sizing by noting that market forecast slides in pitches are largely made-up numbers. He later offers a candid assessment that VCs tend to overstate their value add to founders.12:46–18:14 · Guest teaching 2/10 Founder Due Diligence and the Impact of AngelList Syndicates Harry asks about due diligence and how AngelList syndicates affect traditional VC models. Jon details macro industry changes, including the consolidation of traditional funds and how platforms like AngelList provide deal-flow optionality.18:14–21:05 · Guest teaching 1/10 Inbound Pitch Management and Referral Channels Jon explains his high inbound volume and need for warm referrals, followed by a lighthearted and cooperative quick-fire lightning round.0:59–3:05 · Guest disagreement 0/10 Early Career, Education, and Path to Venture Capital Harry asks a standard conversational opening question about Jon's background and entry into VC. Jon shares an extended backstory about Stanford, working in Taiwan, and receiving advice from Woody Howes to gain operational experience at Microsoft before entering venture capital.3:06–5:10 · Guest disagreement 0/10 Key Lessons and Culture from Microsoft Harry asks straightforward open-ended questions regarding Jon's lessons from Microsoft and key leadership traits. Jon answers cooperatively with general insights on mission clarity and leadership vision.5:10–8:45 · Guest disagreement 1/10 Investment Strategy, Pitch Criteria, and Kitchen Bowl Jon gently corrects Harry's premise regarding his track record, clarifying he has made over 250 investments rather than 100. He then discusses his opportunistic investment approach, including his recent deal in Kitchen Bowl.8:45–12:46 · Guest disagreement 1/10 Evaluating Market Size and Emerging Technologies Jon reframes Harry's question on market sizing by noting that market forecast slides in pitches are largely made-up numbers. He later offers a candid assessment that VCs tend to overstate their value add to founders.12:46–18:14 · Guest disagreement 1/10 Founder Due Diligence and the Impact of AngelList Syndicates Harry asks about due diligence and how AngelList syndicates affect traditional VC models. Jon details macro industry changes, including the consolidation of traditional funds and how platforms like AngelList provide deal-flow optionality.18:14–21:05 · Guest disagreement 0/10 Inbound Pitch Management and Referral Channels Jon explains his high inbound volume and need for warm referrals, followed by a lighthearted and cooperative quick-fire lightning round.0:59–3:05 · Harry pushing back 0/10 Early Career, Education, and Path to Venture Capital Harry asks a standard conversational opening question about Jon's background and entry into VC. Jon shares an extended backstory about Stanford, working in Taiwan, and receiving advice from Woody Howes to gain operational experience at Microsoft before entering venture capital.3:06–5:10 · Harry pushing back 0/10 Key Lessons and Culture from Microsoft Harry asks straightforward open-ended questions regarding Jon's lessons from Microsoft and key leadership traits. Jon answers cooperatively with general insights on mission clarity and leadership vision.5:10–8:45 · Harry pushing back 0/10 Investment Strategy, Pitch Criteria, and Kitchen Bowl Jon gently corrects Harry's premise regarding his track record, clarifying he has made over 250 investments rather than 100. He then discusses his opportunistic investment approach, including his recent deal in Kitchen Bowl.8:45–12:46 · Harry pushing back 0/10 Evaluating Market Size and Emerging Technologies Jon reframes Harry's question on market sizing by noting that market forecast slides in pitches are largely made-up numbers. He later offers a candid assessment that VCs tend to overstate their value add to founders.12:46–18:14 · Harry pushing back 0/10 Founder Due Diligence and the Impact of AngelList Syndicates Harry asks about due diligence and how AngelList syndicates affect traditional VC models. Jon details macro industry changes, including the consolidation of traditional funds and how platforms like AngelList provide deal-flow optionality.18:14–21:05 · Harry pushing back 0/10 Inbound Pitch Management and Referral Channels Jon explains his high inbound volume and need for warm referrals, followed by a lighthearted and cooperative quick-fire lightning round.

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

0:00 · Harry 33.2% · guest 66.8%0:00 · Harry 33.2% · guest 66.8%3:00 · Harry 17.9% · guest 82.1%3:00 · Harry 17.9% · guest 82.1%6:00 · Harry 7.1% · guest 92.9%6:00 · Harry 7.1% · guest 92.9%9:00 · Harry 6.3% · guest 93.7%9:00 · Harry 6.3% · guest 93.7%12:00 · Harry 17.5% · guest 82.5%12:00 · Harry 17.5% · guest 82.5%15:00 · Harry 5% · guest 95%15:00 · Harry 5% · guest 95%18:00 · Harry 12.6% · guest 87.4%18:00 · Harry 12.6% · guest 87.4%21:00 · Harry 95% · guest 5%21:00 · Harry 95% · guest 5%24:00 · Harry 100% · guest 0%24:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 5:26 Correction on Investment Count

Jon directly interrupts Harry's introductory frame to correct his track record from 'over a hundred' to over 250 startup investments.

 Hardest push from Harry ▶ 13:45 Challenging Traditional VC Model

Harry pushes Jon on whether his AngelList syndicate represents a direct threat or structural challenge to traditional VC funds.

 Biggest teaching moment ▶ 8:58 Debunking Hockey Stick Market Slides

Jon educates Harry on why financial market projections in early pitch decks are useless made-up guesses that experienced investors look past.

 Harry holds his own ▶ 13:45 Framing Syndicate Disruption

Harry demonstrates sector knowledge by specifically probing how emerging syndicate dynamics threaten established venture capital structures.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Early Career, Education, and Path to Venture Capital 1100 Harry asks a standard conversational opening question about Jon's background and entry into VC. Jon shares an extended backstory about Stanford, working in Taiwan, and receiving advice from Woody Howes to gain operational experience at Microsoft before entering venture capital.
Key Lessons and Culture from Microsoft 1100 Harry asks straightforward open-ended questions regarding Jon's lessons from Microsoft and key leadership traits. Jon answers cooperatively with general insights on mission clarity and leadership vision.
Investment Strategy, Pitch Criteria, and Kitchen Bowl 1310 Jon gently corrects Harry's premise regarding his track record, clarifying he has made over 250 investments rather than 100. He then discusses his opportunistic investment approach, including his recent deal in Kitchen Bowl.
Evaluating Market Size and Emerging Technologies 1210 Jon reframes Harry's question on market sizing by noting that market forecast slides in pitches are largely made-up numbers. He later offers a candid assessment that VCs tend to overstate their value add to founders.
Founder Due Diligence and the Impact of AngelList Syndicates 2210 Harry asks about due diligence and how AngelList syndicates affect traditional VC models. Jon details macro industry changes, including the consolidation of traditional funds and how platforms like AngelList provide deal-flow optionality.
Inbound Pitch Management and Referral Channels 1100 Jon explains his high inbound volume and need for warm referrals, followed by a lighthearted and cooperative quick-fire lightning round.

Statements from this episode (13)

Insight
Staenberg: Five years of operational experience makes for better venture capitalists
“You can do venture, but why don't you get some real world experience first? Why don't you go somewhere for five years? And actually know what it means to go through cycles, know what it means to hire and fire people, know what it means to have to work on a tea…”
Jon Staenberg May 7, 2015 ▶ 2:16
Assertion Contradicted
Jon Staenberg has invested in over 250 startups
“So it's probably over 250 startups at this point, just to update here.”
Jon Staenberg May 7, 2015 ▶ 5:26
Insight
Staenberg: Co-investor reputation drives VC deals more than the founder's pitch
“Entrepreneurs should know that often it's not about the person you're pitching, but it's about the people you're bringing to the table.”
Jon Staenberg May 7, 2015 ▶ 7:19
Disclosure
Staenberg missed the social media wave while running a wine startup
“That's why I, quite frankly, have probably missed most of what's happened in the whole social media and much of the consumer in the last couple years, partly because I was doing my own startup in the wine business, but also because a lot of what that was about…”
Jon Staenberg May 7, 2015 ▶ 7:55
Insight
Staenberg: Early-stage pitch deck market size projections are made-up guesses
“I don't need to see those numbers because they're made up numbers anyway. They're guesses in many ways.”
Jon Staenberg May 7, 2015 ▶ 9:12
Disclosure
Staenberg invested in DocuSign and Avalara during later funding rounds
“I'm in DocuSign, which I did later in Avalara, Those are two Seattle companies later.”
Jon Staenberg May 7, 2015 ▶ 10:39
Opinion
Staenberg: VCs overvalue their contributions while founders assume all VCs are identical
“Yeah, I think, in general, VCs overvalue their role, and their value add, and but having said that, I think the entrepreneur often makes the mistake of assuming all VCs are the same.”
Jon Staenberg May 7, 2015 ▶ 11:13
Insight
Staenberg: Founders should reference check VCs with failed portfolio company founders
“The tell is asking other companies they've invested in, And not just the ones that have worked out, the ones that didn't work out.”
Jon Staenberg May 7, 2015 ▶ 13:24
Assertion Partly supported
Staenberg: Active major VC funds have dropped from 3,000 to under 1,000
“There used to be close to 3000 major venture funds, and today that's in the hundreds. It's certainly below a thousand.”
Jon Staenberg May 7, 2015 ▶ 14:07
Assertion Partly supported
Staenberg: AngelList and OurCrowd each raised over $100M in 2014
“I think in the last year, both of them had over a hundred million dollars raised through their vehicles.”
Jon Staenberg May 7, 2015 ▶ 15:46
Disclosure
Jon Staenberg discloses his personal investment in AngelList
“For full disclosure, I am an investor in AngelList.”
Jon Staenberg May 7, 2015 ▶ 17:25
Disclosure
Staenberg requires warm introductions or shared investor networks to review pitches
“If someone doesn't come to me through someone I know, Or has a, has an ecosystem of investors that I know, it's very hard for me to take a look at.”
Jon Staenberg May 7, 2015 ▶ 18:51
Disclosure
Staenberg recently invested in recipe app Kitchenbowl and fertility app Kindara
“Well, we talked a little bit about it. Kitchen bowl. Although I also just did a deal called Kindara, which is a mobile app. Yeah, Kindara, which is a women's mobile fertility app. It's both software and hardware.”
Jon Staenberg May 7, 2015 ▶ 20:16
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