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Mar 30, 2016 · 22m · 20vc

20VC: 'The Best Seed Investors Hunt' with Paige Craig @ Arena VC

Paige Craig · 14m spoken Harry Stebbings · 6m spoken
0:00 / 0:00

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Host Harry Stebbings interviews Paige Craig, founder and general partner of Arena Ventures, exploring his transition from the military and intelligence sector to becoming one of Silicon Valley's most active early-stage investors. Craig shares insights on his founder-first thesis, active deal hunting, AngelList syndicates, rapid decision-making, and the dynamics of building successful venture portfolios.

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 3.7 Guest teaching 2.5 Guest disagreement 2.7 Harry pushing back 2.3
05100:0010:0020:002:23–4:37 · Harry as informed peer 2/10 Career Evolution and Founder-Centric Investment Thesis Harry opens with standard biographical questions regarding Paige's transition from the military to venture capital. Paige politely explains his background and how starting with no preconceptions led him to prioritize founder character.4:37–7:18 · Harry as informed peer 3/10 Arena VC's Dual Model and AngelList Syndicates Harry asks about Arena VC's $3.9M fund and dual AngelList syndicate structure. Paige passionately explains the vision of democratizing early-stage investing and attributes syndicate success to shameless self-promotion and strong track record.7:18–9:29 · Harry as informed peer 3/10 Investor Value Addition and Managing Personal Drive Harry asks what makes a great investor and follows up on Paige's admission of entering 'fight mode'. Paige gives a candid, colorful description of VC personality traits ranging from geniuses to 'fucking idiots'.9:29–12:58 · Harry as informed peer 4/10 Crowdfunding Dynamics, AngelList Evolution, and Syndicate Advice Harry questions whether crowdfunding threatens traditional VC and asks for syndicate advice. Paige reframes crowdfunding as just 'one more animal in the kingdom' and forcefully lectures against inexperienced investors using syndicates as 'training wheels'.12:58–15:23 · Harry as informed peer 5/10 Managing Institutional Funds and Active Sourcing as a Hunter Harry cites Paige's recent article on four deal-sourcing methods and asks if being an active 'hunter' is rare for senior VCs. Paige firmly insists that all good early-stage VCs must hunt.15:24–17:57 · Harry as informed peer 5/10 Key Investment Lessons, Decision Speed, and Founder Networks Harry directly challenges Paige's stance on fast decision-making, asking if speed compromises founder evaluation. Paige counters host's premise by turning the question back on Harry and arguing speed depends on evaluator skill.2:23–4:37 · Guest teaching 2/10 Career Evolution and Founder-Centric Investment Thesis Harry opens with standard biographical questions regarding Paige's transition from the military to venture capital. Paige politely explains his background and how starting with no preconceptions led him to prioritize founder character.4:37–7:18 · Guest teaching 1/10 Arena VC's Dual Model and AngelList Syndicates Harry asks about Arena VC's $3.9M fund and dual AngelList syndicate structure. Paige passionately explains the vision of democratizing early-stage investing and attributes syndicate success to shameless self-promotion and strong track record.7:18–9:29 · Guest teaching 2/10 Investor Value Addition and Managing Personal Drive Harry asks what makes a great investor and follows up on Paige's admission of entering 'fight mode'. Paige gives a candid, colorful description of VC personality traits ranging from geniuses to 'fucking idiots'.9:29–12:58 · Guest teaching 3/10 Crowdfunding Dynamics, AngelList Evolution, and Syndicate Advice Harry questions whether crowdfunding threatens traditional VC and asks for syndicate advice. Paige reframes crowdfunding as just 'one more animal in the kingdom' and forcefully lectures against inexperienced investors using syndicates as 'training wheels'.12:58–15:23 · Guest teaching 3/10 Managing Institutional Funds and Active Sourcing as a Hunter Harry cites Paige's recent article on four deal-sourcing methods and asks if being an active 'hunter' is rare for senior VCs. Paige firmly insists that all good early-stage VCs must hunt.15:24–17:57 · Guest teaching 4/10 Key Investment Lessons, Decision Speed, and Founder Networks Harry directly challenges Paige's stance on fast decision-making, asking if speed compromises founder evaluation. Paige counters host's premise by turning the question back on Harry and arguing speed depends on evaluator skill.2:23–4:37 · Guest disagreement 0/10 Career Evolution and Founder-Centric Investment Thesis Harry opens with standard biographical questions regarding Paige's transition from the military to venture capital. Paige politely explains his background and how starting with no preconceptions led him to prioritize founder character.4:37–7:18 · Guest disagreement 1/10 Arena VC's Dual Model and AngelList Syndicates Harry asks about Arena VC's $3.9M fund and dual AngelList syndicate structure. Paige passionately explains the vision of democratizing early-stage investing and attributes syndicate success to shameless self-promotion and strong track record.7:18–9:29 · Guest disagreement 3/10 Investor Value Addition and Managing Personal Drive Harry asks what makes a great investor and follows up on Paige's admission of entering 'fight mode'. Paige gives a candid, colorful description of VC personality traits ranging from geniuses to 'fucking idiots'.9:29–12:58 · Guest disagreement 4/10 Crowdfunding Dynamics, AngelList Evolution, and Syndicate Advice Harry questions whether crowdfunding threatens traditional VC and asks for syndicate advice. Paige reframes crowdfunding as just 'one more animal in the kingdom' and forcefully lectures against inexperienced investors using syndicates as 'training wheels'.12:58–15:23 · Guest disagreement 3/10 Managing Institutional Funds and Active Sourcing as a Hunter Harry cites Paige's recent article on four deal-sourcing methods and asks if being an active 'hunter' is rare for senior VCs. Paige firmly insists that all good early-stage VCs must hunt.15:24–17:57 · Guest disagreement 5/10 Key Investment Lessons, Decision Speed, and Founder Networks Harry directly challenges Paige's stance on fast decision-making, asking if speed compromises founder evaluation. Paige counters host's premise by turning the question back on Harry and arguing speed depends on evaluator skill.2:23–4:37 · Harry pushing back 0/10 Career Evolution and Founder-Centric Investment Thesis Harry opens with standard biographical questions regarding Paige's transition from the military to venture capital. Paige politely explains his background and how starting with no preconceptions led him to prioritize founder character.4:37–7:18 · Harry pushing back 1/10 Arena VC's Dual Model and AngelList Syndicates Harry asks about Arena VC's $3.9M fund and dual AngelList syndicate structure. Paige passionately explains the vision of democratizing early-stage investing and attributes syndicate success to shameless self-promotion and strong track record.7:18–9:29 · Harry pushing back 2/10 Investor Value Addition and Managing Personal Drive Harry asks what makes a great investor and follows up on Paige's admission of entering 'fight mode'. Paige gives a candid, colorful description of VC personality traits ranging from geniuses to 'fucking idiots'.9:29–12:58 · Harry pushing back 2/10 Crowdfunding Dynamics, AngelList Evolution, and Syndicate Advice Harry questions whether crowdfunding threatens traditional VC and asks for syndicate advice. Paige reframes crowdfunding as just 'one more animal in the kingdom' and forcefully lectures against inexperienced investors using syndicates as 'training wheels'.12:58–15:23 · Harry pushing back 3/10 Managing Institutional Funds and Active Sourcing as a Hunter Harry cites Paige's recent article on four deal-sourcing methods and asks if being an active 'hunter' is rare for senior VCs. Paige firmly insists that all good early-stage VCs must hunt.15:24–17:57 · Harry pushing back 6/10 Key Investment Lessons, Decision Speed, and Founder Networks Harry directly challenges Paige's stance on fast decision-making, asking if speed compromises founder evaluation. Paige counters host's premise by turning the question back on Harry and arguing speed depends on evaluator skill.

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

0:00 · Harry 83.1% · guest 16.9%0:00 · Harry 83.1% · guest 16.9%3:00 · Harry 15.8% · guest 84.2%3:00 · Harry 15.8% · guest 84.2%6:00 · Harry 14.3% · guest 85.7%6:00 · Harry 14.3% · guest 85.7%9:00 · Harry 17.9% · guest 82.1%9:00 · Harry 17.9% · guest 82.1%12:00 · Harry 22.5% · guest 77.5%12:00 · Harry 22.5% · guest 77.5%15:00 · Harry 21.9% · guest 78.1%15:00 · Harry 21.9% · guest 78.1%18:00 · Harry 14.6% · guest 85.4%18:00 · Harry 14.6% · guest 85.4%21:00 · Harry 63.9% · guest 36.1%21:00 · Harry 63.9% · guest 36.1%
Sharpest disagreement ▶ 16:09 Paige counters host's premise on diligence speed

When Harry suggests quick decision-making makes evaluating founders harder, Paige directly challenges the host with 'Why do you think it would make it harder?' and attributes evaluation speed to skill level.

 Hardest push from Harry ▶ 16:02 Harry pushes back on quick investment decisions

Harry explicitly challenges Paige's claim that making fast decisions is ideal, asking whether shortening due diligence prevents truly understanding founders.

 Biggest teaching moment ▶ 12:12 Paige lectures on syndicate qualifications

Paige firmly educates listeners against using AngelList syndicates as 'training wheels', arguing that only people with proven experience and personal capital should manage outside funds.

 Harry holds his own ▶ 13:59 Harry cites guest's deal sourcing framework

Harry demonstrates strong background knowledge and preparation by referencing a specific blog post Paige authored on the four differing deal sourcing methods.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Career Evolution and Founder-Centric Investment Thesis 2200 Harry opens with standard biographical questions regarding Paige's transition from the military to venture capital. Paige politely explains his background and how starting with no preconceptions led him to prioritize founder character.
Arena VC's Dual Model and AngelList Syndicates 3111 Harry asks about Arena VC's $3.9M fund and dual AngelList syndicate structure. Paige passionately explains the vision of democratizing early-stage investing and attributes syndicate success to shameless self-promotion and strong track record.
Investor Value Addition and Managing Personal Drive 3232 Harry asks what makes a great investor and follows up on Paige's admission of entering 'fight mode'. Paige gives a candid, colorful description of VC personality traits ranging from geniuses to 'fucking idiots'.
Crowdfunding Dynamics, AngelList Evolution, and Syndicate Advice 4342 Harry questions whether crowdfunding threatens traditional VC and asks for syndicate advice. Paige reframes crowdfunding as just 'one more animal in the kingdom' and forcefully lectures against inexperienced investors using syndicates as 'training wheels'.
Managing Institutional Funds and Active Sourcing as a Hunter 5333 Harry cites Paige's recent article on four deal-sourcing methods and asks if being an active 'hunter' is rare for senior VCs. Paige firmly insists that all good early-stage VCs must hunt.
Key Investment Lessons, Decision Speed, and Founder Networks 5456 Harry directly challenges Paige's stance on fast decision-making, asking if speed compromises founder evaluation. Paige counters host's premise by turning the question back on Harry and arguing speed depends on evaluator skill.

Statements from this episode (12)

Assertion Supported
Craig built and sold a private military business before angel investing
“I built up a private military, sold that business, and about eight years ago, decided to go start working with entrepreneurs”
Paige Craig Mar 30, 2016 ▶ 2:46
Insight
Craig: Founder qualities are the only thing early-stage investors can truly evaluate
“But to me, the, Qualities of the founders are the most important, the most enduring part of any company, and the only thing you can truly understand as an early stage investor”
Paige Craig Mar 30, 2016 ▶ 4:23
Disclosure
Craig provided seed funding to AngelList around 2011
“I seed funded AngelList about five years ago.”
Paige Craig Mar 30, 2016 ▶ 4:54
Insight
Craig: Top AngelList syndicate leads succeed by actively promoting their activity
“I think if you look at any of the other top syndicates out there, you'll find that the people who have top syndicates have gone out there unashamedly and told people, hey, I'm doing this, set my flag”
Paige Craig Mar 30, 2016 ▶ 6:39
Opinion
Craig: Venture capitalists range from geniuses to 'fucking idiots'
“VCs are just people, so you'll find VCs who are very intellectual, some VCs are very diplomatic, some VCs are very aggressive, some VCs are fucking idiots, some VCs are genius”
Paige Craig Mar 30, 2016 ▶ 9:01
Prediction Held up
Craig: Syndicate leads will use AngelList for Series A and B rounds
“A hundred percent. I think it, you know, it's not necessarily that AngelList moves into it, it's that the syndicate leads and other players will use AngelList to do pre-seed, to do seed, to do A, to do B.”
Paige Craig Mar 30, 2016 ▶ 11:11
Insight
Craig: Backing syndicates requires investing across a full portfolio
“But at the end of the day, if you're going to go back syndicates, it's a portfolio play. So go find a syndicate lead or two that you like and try to back as many deals as possible.”
Paige Craig Mar 30, 2016 ▶ 11:56
Insight
Craig: Unproven investors have no business launching syndicates or venture funds
“If you're going to start a syndicate, please do it once you have some real fucking experience, because there's a lot of people start syndicates who have no business doing so, but it's the same with people who start funds and have no business doing so. If you'r…”
Paige Craig Mar 30, 2016 ▶ 12:14
Insight
Craig: All good seed-stage investors actively hunt for deals
“I know that the good ones who are early stage are hunters because, you know, if you're further up the ecosystem, if you're a, Series A, Series B, VC. Obviously, all the great founders have been funded by someone. So you're going to, you know, naturally a lot o…”
Paige Craig Mar 30, 2016 ▶ 14:46
Insight
Craig: 3 to 8 hours of founder meetings is enough for diligence
“Three hours, six hours, eight hours of meeting with people. But that's plenty of time to understand if these are the people that we want to invest. It's spending a week with a new team is a lot of time.”
Paige Craig Mar 30, 2016 ▶ 16:38
Disclosure
Craig wrote the very first check into Wish.com
“I wrote Probably the first, the very first check into a company back then known as context logic, which is now wish.com. And they're a very large e-commerce play now, billions of dollars that came from an introduction from Brian Wong of keep.”
Paige Craig Mar 30, 2016 ▶ 17:01
Opinion
Craig: Government is deeply dysfunctional but ripe for startup disruption
“I think government is absolutely horrible and screwed up, and it's hard to imagine how a for-profit company can go disrupt it, but I'm very open to Founders who are disrupting government.”
Paige Craig Mar 30, 2016 ▶ 19:51
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