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Feb 4, 2020 · 39m · 20vc

Breaking News: Meet First Round Capital's Newest Partner, How To Approach Generational Transition as a Venture Firm & The Dangers of Attribution In Venture

Todd Jackson · 15m spoken Harry Stebbings · 11m spoken Phin Barnes · 10m spoken
0:00 / 0:00

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In Episode 2800 of The 20 Minute VC, Harry Stebbings hosts First Round Capital partners Phin Barnes and Todd Jackson to announce Jackson's new role as Venture Partner. The discussion explores Jackson's product background at top tech companies like Google and Dropbox, frameworks for finding product-market fit, the transition from operator to investor, and First Round's unique firm culture.

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 30% of the talking time here. How this is scored →

Harry as informed peer 3.8 Guest teaching 3.3 Guest disagreement 1.2 Harry pushing back 1.8
05100:0010:0020:0030:003:08–6:56 · Harry as informed peer 2/10 Exclusive Announcement: Todd Jackson Joins First Round Capital Harry welcomes both guests for a special dual-guest interview and sets up the announcement. Phin officially announces Todd Jackson joining First Round Capital as a venture partner, after which Todd details his career history across Google, Facebook, Twitter, and Dropbox.6:56–12:39 · Harry as informed peer 3/10 Navigating the Balance Between Learning and Execution in Venture Phin offers advice to Todd on balancing learning with doing when entering a venture firm. Todd outlines key lessons from Google, Dropbox, and Facebook, highlighting product development rigor and transitioning from consumer to SaaS.12:40–16:58 · Harry as informed peer 6/10 Evaluating Unit Economics and the Framework for Product-Market Fit Harry challenges the practice of seed investors evaluating early LTV to CAC ratios before product-market fit exists. Phin agrees, and Todd shares First Round's framework for evaluating product-market fit.16:58–19:40 · Harry as informed peer 4/10 Transitioning from Operator to Effective Venture Investor and Coach Harry asks Todd how his background as an operator influences his approach to advising founders. Todd explains the transition from trying to answer all problems himself to acting as an empathetic listener and coach.19:40–30:20 · Harry as informed peer 5/10 Managing Generational Transitions and Culture at First Round Capital Harry asks a direct question about partner transitions and leadership changes at First Round. Phin details how First Round avoids internal politics by eschewing individual portfolio attribution models in favor of a firm-wide team approach.30:24–36:26 · Harry as informed peer 3/10 Quick-Fire Insights: Book Recommendations, Pitch Dynamics, and Portfolio Wins In the quick-fire section, guests share book picks and career reflections. Phin strongly rejects the common startup advice that ideas don't matter, calling the claim complete garbage.3:08–6:56 · Guest teaching 2/10 Exclusive Announcement: Todd Jackson Joins First Round Capital Harry welcomes both guests for a special dual-guest interview and sets up the announcement. Phin officially announces Todd Jackson joining First Round Capital as a venture partner, after which Todd details his career history across Google, Facebook, Twitter, and Dropbox.6:56–12:39 · Guest teaching 5/10 Navigating the Balance Between Learning and Execution in Venture Phin offers advice to Todd on balancing learning with doing when entering a venture firm. Todd outlines key lessons from Google, Dropbox, and Facebook, highlighting product development rigor and transitioning from consumer to SaaS.12:40–16:58 · Guest teaching 3/10 Evaluating Unit Economics and the Framework for Product-Market Fit Harry challenges the practice of seed investors evaluating early LTV to CAC ratios before product-market fit exists. Phin agrees, and Todd shares First Round's framework for evaluating product-market fit.16:58–19:40 · Guest teaching 3/10 Transitioning from Operator to Effective Venture Investor and Coach Harry asks Todd how his background as an operator influences his approach to advising founders. Todd explains the transition from trying to answer all problems himself to acting as an empathetic listener and coach.19:40–30:20 · Guest teaching 4/10 Managing Generational Transitions and Culture at First Round Capital Harry asks a direct question about partner transitions and leadership changes at First Round. Phin details how First Round avoids internal politics by eschewing individual portfolio attribution models in favor of a firm-wide team approach.30:24–36:26 · Guest teaching 3/10 Quick-Fire Insights: Book Recommendations, Pitch Dynamics, and Portfolio Wins In the quick-fire section, guests share book picks and career reflections. Phin strongly rejects the common startup advice that ideas don't matter, calling the claim complete garbage.3:08–6:56 · Guest disagreement 0/10 Exclusive Announcement: Todd Jackson Joins First Round Capital Harry welcomes both guests for a special dual-guest interview and sets up the announcement. Phin officially announces Todd Jackson joining First Round Capital as a venture partner, after which Todd details his career history across Google, Facebook, Twitter, and Dropbox.6:56–12:39 · Guest disagreement 0/10 Navigating the Balance Between Learning and Execution in Venture Phin offers advice to Todd on balancing learning with doing when entering a venture firm. Todd outlines key lessons from Google, Dropbox, and Facebook, highlighting product development rigor and transitioning from consumer to SaaS.12:40–16:58 · Guest disagreement 1/10 Evaluating Unit Economics and the Framework for Product-Market Fit Harry challenges the practice of seed investors evaluating early LTV to CAC ratios before product-market fit exists. Phin agrees, and Todd shares First Round's framework for evaluating product-market fit.16:58–19:40 · Guest disagreement 0/10 Transitioning from Operator to Effective Venture Investor and Coach Harry asks Todd how his background as an operator influences his approach to advising founders. Todd explains the transition from trying to answer all problems himself to acting as an empathetic listener and coach.19:40–30:20 · Guest disagreement 1/10 Managing Generational Transitions and Culture at First Round Capital Harry asks a direct question about partner transitions and leadership changes at First Round. Phin details how First Round avoids internal politics by eschewing individual portfolio attribution models in favor of a firm-wide team approach.30:24–36:26 · Guest disagreement 5/10 Quick-Fire Insights: Book Recommendations, Pitch Dynamics, and Portfolio Wins In the quick-fire section, guests share book picks and career reflections. Phin strongly rejects the common startup advice that ideas don't matter, calling the claim complete garbage.3:08–6:56 · Harry pushing back 0/10 Exclusive Announcement: Todd Jackson Joins First Round Capital Harry welcomes both guests for a special dual-guest interview and sets up the announcement. Phin officially announces Todd Jackson joining First Round Capital as a venture partner, after which Todd details his career history across Google, Facebook, Twitter, and Dropbox.6:56–12:39 · Harry pushing back 0/10 Navigating the Balance Between Learning and Execution in Venture Phin offers advice to Todd on balancing learning with doing when entering a venture firm. Todd outlines key lessons from Google, Dropbox, and Facebook, highlighting product development rigor and transitioning from consumer to SaaS.12:40–16:58 · Harry pushing back 5/10 Evaluating Unit Economics and the Framework for Product-Market Fit Harry challenges the practice of seed investors evaluating early LTV to CAC ratios before product-market fit exists. Phin agrees, and Todd shares First Round's framework for evaluating product-market fit.16:58–19:40 · Harry pushing back 1/10 Transitioning from Operator to Effective Venture Investor and Coach Harry asks Todd how his background as an operator influences his approach to advising founders. Todd explains the transition from trying to answer all problems himself to acting as an empathetic listener and coach.19:40–30:20 · Harry pushing back 4/10 Managing Generational Transitions and Culture at First Round Capital Harry asks a direct question about partner transitions and leadership changes at First Round. Phin details how First Round avoids internal politics by eschewing individual portfolio attribution models in favor of a firm-wide team approach.30:24–36:26 · Harry pushing back 1/10 Quick-Fire Insights: Book Recommendations, Pitch Dynamics, and Portfolio Wins In the quick-fire section, guests share book picks and career reflections. Phin strongly rejects the common startup advice that ideas don't matter, calling the claim complete garbage.

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

0:00 · Harry 100% · guest 0%0:00 · Harry 100% · guest 0%3:00 · Harry 32.8% · guest 67.2%3:00 · Harry 32.8% · guest 67.2%6:00 · Harry 26.4% · guest 73.6%6:00 · Harry 26.4% · guest 73.6%9:00 · Harry 0% · guest 100%9:00 · Harry 0% · guest 100%12:00 · Harry 29.8% · guest 70.2%12:00 · Harry 29.8% · guest 70.2%15:00 · Harry 10.5% · guest 89.5%15:00 · Harry 10.5% · guest 89.5%18:00 · Harry 16.3% · guest 83.7%18:00 · Harry 16.3% · guest 83.7%21:00 · Harry 8.1% · guest 91.9%21:00 · Harry 8.1% · guest 91.9%24:00 · Harry 28% · guest 72%24:00 · Harry 28% · guest 72%27:00 · Harry 1.5% · guest 98.5%27:00 · Harry 1.5% · guest 98.5%30:00 · Harry 28% · guest 72%30:00 · Harry 28% · guest 72%33:00 · Harry 17% · guest 83%33:00 · Harry 17% · guest 83%36:00 · Harry 92.5% · guest 7.5%36:00 · Harry 92.5% · guest 7.5%39:00 · Harry 100% · guest 0%39:00 · Harry 100% · guest 0%
Sharpest disagreement ▶ 34:29 Phin rejects 'ideas don't matter' mantra

Phin forcefully calls common venture advice garbage, arguing that early ideas carry the core energy and vision that propel startups forward.

 Hardest push from Harry ▶ 12:40 Harry challenges early-stage LTV/CAC obsession

Harry calls out seed investors who obsess over undefined LTV to CAC ratios, asking directly whether it is short-sighted to ignore them at the pre-seed stage.

 Biggest teaching moment ▶ 8:33 Todd details Google's rigorous product standards

Todd educates Harry on Google's internal UI review process, recounting how Gmail delayed a major release over a tiny 30 millisecond latency increase.

 Harry holds his own ▶ 12:40 Harry asserts his perspective on seed metric irrelevance

Harry confidently expresses frustration with seed investors fixating on metrics that are fundamentally unpredictable at the pre-launch stage.
the scores for every segment, with the reasoning behind each
ChapterTopicHarry as informed peerGuest teachingGuest disagreementHarry pushing backWhy
Exclusive Announcement: Todd Jackson Joins First Round Capital 2200 Harry welcomes both guests for a special dual-guest interview and sets up the announcement. Phin officially announces Todd Jackson joining First Round Capital as a venture partner, after which Todd details his career history across Google, Facebook, Twitter, and Dropbox.
Navigating the Balance Between Learning and Execution in Venture 3500 Phin offers advice to Todd on balancing learning with doing when entering a venture firm. Todd outlines key lessons from Google, Dropbox, and Facebook, highlighting product development rigor and transitioning from consumer to SaaS.
Evaluating Unit Economics and the Framework for Product-Market Fit 6315 Harry challenges the practice of seed investors evaluating early LTV to CAC ratios before product-market fit exists. Phin agrees, and Todd shares First Round's framework for evaluating product-market fit.
Transitioning from Operator to Effective Venture Investor and Coach 4301 Harry asks Todd how his background as an operator influences his approach to advising founders. Todd explains the transition from trying to answer all problems himself to acting as an empathetic listener and coach.
Managing Generational Transitions and Culture at First Round Capital 5414 Harry asks a direct question about partner transitions and leadership changes at First Round. Phin details how First Round avoids internal politics by eschewing individual portfolio attribution models in favor of a firm-wide team approach.
Quick-Fire Insights: Book Recommendations, Pitch Dynamics, and Portfolio Wins 3351 In the quick-fire section, guests share book picks and career reflections. Phin strongly rejects the common startup advice that ideas don't matter, calling the claim complete garbage.

Statements from this episode (10)

Assertion Supported
Gmail grew to 200 million users during Todd Jackson's tenure
“And we grew Gmail to over two hundred million users during my time there.”
Todd Jackson Feb 4, 2020 ▶ 4:52
Assertion Partly supported
Cover reached 2M organic users and sold to Twitter in 14 months
“We grew to over two million users in our first couple months with zero money spent on paid acquisition, and we got acquired by Twitter just 14 months after founding the company.”
Todd Jackson Feb 4, 2020 ▶ 5:34
Insight
New hires in learning mode miss early opportunities for impact
“So I think there can be a bias when you join a team, and especially it's exacerbated when you join a small, close-knit team, frankly, in a role that you've never held before. And the bias is to shift into a hundred percent learning mode. And when you do that, …”
Phin Barnes Feb 4, 2020 ▶ 7:23
Assertion Not publicly verifiable
Google delayed a major Gmail redesign over 30 milliseconds of latency
“And I remember one time we had gone through this big redesign of the label system in Gmail, and we were about to launch it. And actually the night before launch, we held it back because we realized we had unintentionally added about 30 milliseconds or 40 milli…”
Todd Jackson Feb 4, 2020 ▶ 9:28
Assertion Not publicly verifiable
Dropbox maintained a double-digit LTV:CAC ratio prior to its 2018 IPO
“At Dropbox, you know, the LTV to CAC Ratio was actually in the double digits when I was there, and so that enabled us to have the revenue predictability that was key to our IPO in 2018, and it was just a few years after we pivoted most of the business from con…”
Todd Jackson Feb 4, 2020 ▶ 10:59
Assertion Not checkable as stated
Over half of First Round Capital's investments come from founder referrals
“Similar to over half of our investments, Todd was referred to us by another founder that we'd already partnered with, Dave Gerard from Upstart.”
Phin Barnes Feb 4, 2020 ▶ 21:25
Disclosure
Todd Jackson is an LP in funds by Stanton, Ling, and Kimmel
“I've gotten to see a lot of my friends who are great investors. Katie Stanton, like you mentioned, love, love the episode with her, by the way, Ben Ling, Brianne Kimmel start their own funds as solo GPs. And I'm actually an LP in those funds.”
Todd Jackson Feb 4, 2020 ▶ 25:32
Disclosure
First Round Capital does not use deal attribution or partner portfolios
“We don't have an attribution model, and so when we make an investment, it's a first-round company. I don't have my portfolio, and over time, Todd won't have his, and so on.”
Phin Barnes Feb 4, 2020 ▶ 28:04
Insight
First-year VC partner success is measured by influencing the partnership
“It's a hard question, because of course, it's a long-term game, and given we form our partnerships with founders at the earliest stages, a new partner, you certainly won't be able to measure returns for some time. So for me, it's really about being able to mov…”
Phin Barnes Feb 4, 2020 ▶ 32:51
Opinion
Phin Barnes: Saying startup ideas don't matter drives me crazy
“I think recently when I hear people say ideas don't matter, it just drives me crazy. Like the idea is the most valuable thing you have when you start, and the best ones are the result of a tremendous amount of work and effort, experience, insight. They're uniq…”
Phin Barnes Feb 4, 2020 ▶ 34:30
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