20VC: First Round’s Josh Kopelman on Why Price Is Both An Art and A Science, Why Ownership Must Be Built on First Check and The Negative Consequences of Attribution in Venture

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Josh Kopelman is Founder & Partner @ First Round, one of the world’s leading seed funds with a portfolio including the likes of Uber, Warby Parker, Flatiron Health, Square, HotelTonight, GOAT and more incredible companies. As for Josh, he founded First Round in 2004 to reinvent seed stage investing. Since he has invested in over 200 startups and been ranked 4th in Forbes Midas List and named one of the top ten ‘angel investors’ in the US by Newsweek magazine. Josh has previously sat on the boards of Flatiron Health, Clover Health, AppNexus and more. 

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In Today’s Episode You Will Learn:

1.) How Josh made his way into the wonderful world of venture from angel investing and what the inspiration behind the founding of First Round was?

2.) How does Josh think about price sensitivity today? What were his learnings from being priced out of the seed round for Twitter and Dropbox? How has Josh seen his relationship to price change over time? How did witnessing the boom and bust both as operator and investor affect his investing mentality today?

3.) How does Josh and First Round think about reserve allocation? How has their thinking changed and evolved over time? Does Josh believe that ownership is fundamentally built on first check? What does the investment decision-making process look like for reserves? In terms of allocation, how does Josh think about time allocation across portfolio? Spend it with the winners, they return the fund or the strugglers and save cents on the dollar?

4.) Josh has spent over 3,000 hours on boards, what have been some of the biggest inflection points that have changed the way he thinks about being a good board member? How has he seen his style and approach change over time? What advice would Josh give to an individual that has just gained their first institutional board seat?

5.) Why does Josh believe that we fundamentally neglect “the pick” today in startup world? Why does Josh believe a high degree of startup mortality begins at the pick (idea) stage? How do the very best founders aproach this stage? How should these founders approach picking their investors? What should they look for? What should they be wary of?

6.) Why does Josh want to be known as a better picker of partners than investments? How has Josh thought about the building ou of the first round partnership over time? If there was anything he would have done differently, what would it be? Why does Josh fundamentally disagree with attribution? How does Josh think about generational transition? What are the steps required to do it well?

Items Mentioned In Today’s Show:

Josh’s Fave Book: Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts

As always you can follow HarryThe Twenty Minute VC and Joel on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

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20VC: Sequoia’s Pat Grady on What Sequoia Is Focused On Today, How Sequoia Think About Investment Decision-Making Processes & Why It Is Important To Trade A Few Points of Efficiency for Culture When It Comes To Attribution

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Pat Grady is a Partner @ Sequoia, one of the world’s leading and most renowned venture firms with a portfolio including WhatsApp, Zoom, Stripe, Airbnb, Github and many more incredible companies. As for Pat, at Sequoia he co-leads the firms growth investment team and has been involved with some of the true greats, Hubspot, Zoom, Okta, Qualtrics, the list goes on. Prior to Sequoia Pat spent three years with Summit Partners.

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In Today’s Episode You Will Learn:

1.) How Pat made his way from Summit Partners to co-leading Sequoia’s growth investment team? Was it intimidating for Pat entering a partnership with Jim Goetz, Don Valentine, Roelof Botha? How did he manage those nerves?

2.) So many different funds and activities, so what is Sequoia focused on today? Where does Sequoia think about their ideal insertion point today? How do they see the deployment of their blended capital across rounds? Does Pat believe in ownership on first check or building ownership over time? How does Pat think about the extended window of privatisation with IPOs being continuously delayed?

3.) Does Pat believe that VC really is a team sport today? Does Pat agree with Josh Kopelman’s statement, “I would rather be a better picker of partners than investments”? What are the core requirements, skills and traits that Sequoia looks for when adding to their partnership?

4.) What is the investment decision-making process at Sequoia? How do they feel about unanimity vs conviction based investment decisions? What are the pros and cons of each? What does Pat believe is the most non-obvious investment decision that Sequoia have made? Sequoia run an incredibly rigorous process when investing, how does Pat balance between that level of rigour with the speed to win the deal?

5.) What advice would Pat give to someone that has just gained their first institutional board? What does Pat know now that he wishes he had known when he started in VC? How does Pat think about time allocation across the portfolio? Concentrate on winners or the strugglers are where your reputation is built? Leading Sequoia Growth and with a beautiful family, how does Pat approach work/life balance?

Items Mentioned In Today’s Show:

Pat’s Fave Book: God Friended Me

Pat’s Most Recent Investment: Embark: Revolutionizing Commercial Transport 

As always you can follow HarryThe Twenty Minute VC and Pat on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

20VC Books

Anjney Midha’s Fave Book: Rainbows End Sam Lessin’s Fave Book: Lessons of History Joel Flory’s Fave Book: How To Talk So Kids Will Listen and Listen So Kids Will Talk  Josh Kopelman’s Fave Book: Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts Olof Mathe’s Fave Book: SPQR: A History of Ancient Rome Hunter Somerville’s Fave Book: Great Expectations by Charles Dickens

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20VC: First Round’s Phin Barnes on How The Best Founders Optimize for Learning Per Dollar Spent, What Makes A Truly Special Founder/VC Relationship and Why Pattern Recognition is Another Term For Intellectual Laziness

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Phin Barnes is a Partner @ First Round Capital, one of the most prestigious and successful early-stage funds of the last decade with a portfolio including the likes of Uber, Square, Warby Parker, HotelTonight, GOAT, PatientPing, Atrium and more incredible companies. As for Phin, in his own words, he learned the business of startups helping grow AND1 from $15M to $225M in revenue as Creative Director for Footwear, and started his own fitness video-game company, producing Yourself!Fitness, the first game of its kind for Xbox and PlayStation 2 where he built partnerships with the likes of Procter & Gamble and McDonald’s. Phin also writes the most fantastic blog, sneakerheadVC, that really is a must read.

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In Today’s Episode You Will Learn:

1.) How Phin came to be a Partner @ First Round by working for free, with no plans to be a Partner?

2.) What were Phin’s biggest lessons from learning from and observing Josh Kopelman? How does Phin define true success as a VC today? Why is the model of determining success according to returns fundamentally flawed? How does Phin approach the need for VCs to be both curious and competitive? What is the nuance there?

3.) Why does Phin believe that the commonly discussed “pattern recognition” is another term for intellectual laziness? What does Phin do to prevent his forming assumptions on the founders he meets? Why does Phin fundamentally disagree with the common VC habit of looking for weaknesses in founders?

4.) Does Phin agree that we have an oversupply of capital in market today? How does Phin determine when a stretch on price is a stretch too far? Why does Phin think that more emphasis should be placed on the business model that VCs have? What does Phin mean when he says that he is on the “sell side”?

5.) What does Phin mean when he says that “VCs should focus on a founders ability to optimise for learning per dollar spent”? Is cash ever a defensible moat in it’s own right? What does Phin believe is the right way for founders to use capital as a weapon?

6.) How does Phin and First Round think about the right way to allocate reserves effectively? What does that look like in reality? What does the decision-making process look like on re-investments? Why does Phin believe that the framework of “pro-rata is largely lazy?

Items Mentioned In Today’s Show:

Phin’s Fave Book: Writing Down the Bones: Freeing the Writer WithinBoyd: The Fighter Pilot Who Changed the Art of War

Phin’s Most Recent Investment: Ubiquity6

As always you can follow HarryThe Twenty Minute VC and Phin on Twitter here!

Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

 

20VC: Why Companies Going Bust Is Part Of The Plan, Why Most VCs Are Later Stage Than They Think & Why Venture Capital Is Humbling with Charlie O’Donnell, Founder @ Brooklyn Bridge Ventures

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Charlie O’Donnell is the Founder and Sole Partner @ Brooklyn Bridge Ventures, the first venture capital fund based in Brooklyn, who manage $23m across 2 funds. Prior to founding Brooklyn Bridge, Charlie worked at the prestigious First Round Capital, with the likes of Josh Koppelman and Union Square Ventures with Fred Wilson. If that wasn’t enough Charlie is one of only a dozen to be named to Business Insider’s 100 Most Influential People in NY Tech five or more times and has served on the founding board of the New York Tech Meetup and is one of the group’s first 100 members. His blog, This is Going to Be BIG!, is one of the ten most widely read VC blogs in the country with over 8,000 readers.

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In Today’s Episode You Will Learn:

1.) How Charlie made his move from college to venture and then struck out on his own from USV?

2.) Charlie has previously said that ‘venture capital is humbling’. How does Charlie look to construct his portfolio with Brooklyn Bridge? How does he come to terms with the fact he will be wrong most of the time?

3.) What are Charlie’s views towards follow-on funding and allocating reserves of the fund? How important is this from a return multiple perspective? How much of a difference does it make for founders to raise a next round with 100% of seed investors committed?

4.) Charlie has previously suggested the importance of being helpful and hard working. Is that really enough to build a brand in today’s competitive VC environment? Is brand a form of defensible IP?

5.) How does Charlie react to Ben Lerer’s suggestion that Jet.com and Dollar Shave Club are the first dominoes of an incoming wave of e-commerce M&A?

Items Mentioned In Today’s Show:

Charlie’s Fave Blog: Wait But Why

Charlie’s Most Recent Investment: Industrial Organic

As always you can follow Harry, The Twenty Minute VC and Charlie on Twitter here!

Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC.

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20 VC 043: How To Be A VC Analyst and Lessons From Union Square and First Round with Charlie O’Donnell, Founder @ Brooklyn Bridge Venture

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Charlie O’Donnell is the Founder and Sole Partner @ Brooklyn Bridge Ventures, the first venture capital fund based in Brooklyn. Prior to founding Brooklyn Bridge, Charlie worked at the prestigious First Round Capital, with the likes of Josh Koppelman and Union Square Ventures with Fred Wilson. If that wasn’t enough Charlie is one of only a dozen to be named to Business Insider’s 100 Most Influential People in NY Tech five or more times and has served on the founding board of the New York Tech Meetup and is one of the group’s first 100 members. His blog, This is Going to Be BIG!, is one of the ten most widely read VC blogs in the country with over 8,000 readers.

Among the many discussions Harry and Charlie delve into how to enter the VC job industry, how the seed stage fund raising environment is behaving, what Charlie learnt from Union Square and First Round, tactics that individuals can do to increase their own branding, Charlie’s views on investing in hardware, investing in Kickstarter backed companies, the next five years for Charlie, what has blown Charlie’s mind in the last four weeks, the marketing possibilities of Instagram for startups and much more…

 

Items Mentioned in Today’s Show: