VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143
Today’s show:
In this powerhouse VC roundtable, @Jason sits down with Sequoia’s Doug Leone and Cyberstarts’ Gili Raanan to share brutally honest insights on startup recruiting, evaluating second-time founders, and how to truly find product-market fit. They break down why big-tech résumés can be misleading, how to structure early teams, and what separates “missionary” talent from mercenaries. Plus, the myth of early ARR, the art of founder-board trust, and how AI is (and isn’t) reshaping startup velocity. Must-watch for founders, VCs, and anyone building from 0 to 1.
Timestamps:
(03:25) The origins of Wiz and how VCs know when to invest
(05:17) What qualities are investors looking for in founders and entrepreneurs?
(09:53) LinkedIn Ads - Get a $100 LinkedIn ad credit at http://www.linkedin.com/thisweekinstartups
(18:40) How to know when you’ve reached true Product Market Fit: the experts sound off
(19:20) Notion - Try it for free today at https://notion.com/twist
(25:39) The secrets of recruiting top talent
(29:54) CLA - Get started with CLA's CPAs, consultants, and wealth advisors now at https://claconnect.com/tech
(39:38) Judging a startup’s revenue quality and “founder vs. salesman” deals
(53:38) Is venture capital kind of a SCAM?
(55:00) Seed Investing: “Pick them right and early”
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Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are N of one conversations with N of one people. There's nobody I've met quite like Doug Leone.
Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him.
We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear.
I listen to this at least once a year. I hope you enjoy it.
Subscribe to Colossus Review.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Show Notes
[00:00:00] Welcome to Invest Like the Best
[00:05:21] What Don Valentine’s heart was like
[00:08:30] The most productive and unproductive parts of Don’s toughness
[00:12:55] Why it’s so important to understand someone’s core motivations
[00:18:44] The most formative experiences he had prior to becoming an investor that impacted his investing the most
[00:22:37] What venture looks like to him today relative to his prior career
[00:28:37] Whether or not he’d go into venture today if he was in his late 20s
[00:34:10] Helping companies circumnavigate mediocre positioning
[00:39:15] How interacting with companies early on has changed over the ears
[00:43:12] Whether or not new entrants into venture should build firms with enterprise value
[00:48:14] Sussing out the killer gene in somebody
[00:51:04] How successful people can instill the lessons learned from hardship into their children
[00:54:30] Whether or not competitive advantage can be architected ahead of time when building a company
[00:57:21] The early 2000s clawback at Sequoia and what navigating that period was like
[01:01:06] What he’s learned about picking the right LPs and partnering with them
[01:04:18] Making sure that performance is on everyone’s minds all the time
[01:09:59] The kindest thing anyone has ever done for him
20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When to Pay Up vs When to Stay Disciplined, The Biggest Lessons on Price Discipline from 8 of the World's Best Investors
Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.
Marcelo Claure is the Founder & CEO of Claure Group, a multi-billion-dollar global investment firm. He is the Executive Chairman and Managing Partner of Bicycle Capital, a $500M Latin America-focused growth equity fund, and was appointed Chairman in Latin America of SHEIN, the global #1 on-demand fashion company in the world. Claure was also the CEO of SoftBank Group International where he launched SoftBank's $8B Latin America Funds, and had direct oversight for SoftBank's operating companies.
Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel.
Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets.
Martín Escobari is Co-President, Managing Director and Head of General Atlantic's business in Latin America. Martín is Chairman of the firm's Investment Committee and also serves on the Management and Portfolio Committees.
Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo's early entry into software buyouts and built the firm into one of the top private equity firms in the world.
In Today's Episode on Price Sensitivity We Discuss:
Doug Leone: Why the attitude of "deploy, deploy, deploy will get so many in trouble"?
Marcelo Claure: How to know when price matters and when it does not?
Geoff Lewis: What is the right framework to assess price at an early stage?
David Tisch: How does the importance of price change vis a vis company vs portfolio?
Orlando Bravo: What have been Thoma Bravo's biggest lessons on price?
Cyan Banister: Why does Cyan believe there will be a reckoning?
Doug Leone - Lessons from a Titan - [Invest Like the Best, REPLAY]
This week we are replaying our episode with Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone.
Listen to Founders Podcast
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.
Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Show Notes
[00:03:21] - [First question] - What Don Valentine’s heart was like
[00:06:30] - The most productive and unproductive parts of Don’s toughness
[00:10:55] - Why it’s so important to understand someone’s core motivations
[00:14:18] - Questions or topics he returns to when getting to know people
[00:16:44] - The most formative experiences he had prior to becoming an investor that impacted his investing the most
[00:20:37] - What venture looks like to him today relative to his prior career
[00:23:51] - His style of approaching emerging technology markets like AI as an investor
[00:26:37] - Whether or not he’d go into venture today if he was in his late 20s
[00:28:30] - Commonalities between the very best at going to market effectively
[00:31:11] - The key components of great product positioning
[00:37:15] - How interacting with companies early on has changed over the ears
[00:41:12] - Whether or not new entrants into venture should build firms with enterprise value
[00:46:14] - Sussing out the killer gene in somebody
[00:49:04] - How successful people can instill the lessons learned from hardship into their children
[00:53:52] - Whether or not his view on competitive advantage has changed
[00:55:21] - The early 2000s clawback at Sequoia and what navigating that period was like
[01:00:40] - The most interesting question an LP has ever asked him
[01:05:00] - Which dinner companions he’d pick to educate a newly successful founder
[01:07:59] - The kindest thing anyone has ever done for him
Doug Leone - Lessons from a Titan - [Invest Like the Best, EP.318]
My guest this week is Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone.
For the full show notes, transcript, and links to mentioned content, check out the episode page here.
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This episode is brought to you by Tegus, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.
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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.
Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.
Follow us on Twitter: @patrick_oshag | @JoinColossus
Show Notes
[00:03:21] - [First question] - What Don Valentine’s heart was like [00:06:30] - The most productive and unproductive parts of Don’s toughness
[00:09:01] - Being the opposite of insufferable and how it was different when he was younger
[00:10:55] - Why it’s so important to understand someone’s core motivations
[00:14:18] - Questions or topics he returns to when getting to know people
[00:15:31] - How much time he believes it can take to really get to know someone
[00:20:37] - What venture looks like to him today relative to his prior career
[00:23:51] - His style of approaching emerging technology markets like AI as an investor
[00:26:37] - Whether or not he’d go into venture today if he was in his late 20s
[00:28:30] - Commonalities between the very best at going to market effectively
[00:31:11] - The key components of great product positioning
[00:32:10] - Helping companies circumnavigate mediocre positioning
[00:33:25] - Generating demand and leads and doing it well
[00:37:15] - How interacting with companies early on has changed over the ears
[00:46:14] - Sussing out the killer gene in somebody
[00:47:25] - What high school was like for him when he first came to the US
[00:49:04] - How successful people can instill the lessons learned from hardship into their children
[00:50:45] - The most common failure modes he’s seen for investors
[00:55:21] - The early 2000s clawback at Sequoia and what navigating that period was like
[00:59:06] - What he’s learned about picking the right LPs and partnering with them
[01:00:40] - The most interesting question an LP has ever asked him
[01:02:18] - Making sure that performance is on everyone’s minds all the time
[01:04:04] - What the components of a fantastic investment memo are
[01:05:00] - Which dinner companions he’d pick to educate a newly successful founder
[01:05:29] - What first popped out at him as black magic when he started investing
[01:07:59] - The kindest thing anyone has ever done for him
20VC: The Memo: Bill Gurley, Doug Leone, Keith Rabois; Investing Lessons from Prior Busts, How Their Investor Psychology Changed, What Can Be Applied To Today's Market
Bill Gurley is a General Partner @ Benchmark Capital, Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow.
Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more.
Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on.
Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades.
Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade.
Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify and many more incredible companies.
Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and many more.
In Today's Episode You Will Learn:
1.) How does the current environment compare to prior busts?
2.) How will the changing interest rates impact the startup funding climate moving forward?
3.) Why is the rate of inflation the only true metric which reveals the ultimate fate of the economy?
4.) What are the world's leading investors telling their founders?
5.) How are the best investors in the world thinking through reserves management?
Doug Leone of Sequoia Capital: global growth, partnering with legendary companies and the evergreen fund | E1403
"Sequoia Capital is the greatest venture capital firm of all time. It's indisputable." - Jason
Jason chats with Sequoia's Doug Leone, a leader who shepherded the firm for four decades. They discuss great founders, governance, Sequoia's global expansion, mentoring the next generation of investors and more.
(00:00) Jason intros today’s legendary interview w/ Doug Leone of Sequoia Capital
(01:14) When Doug Leone got his start
(11:00) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://Squarespace.com/TWIST
(12:23) The impact selling secondary shares has on founders
(15:43) “The founder’s job is to make the receptionist rich”
(21:14) First Republic Bank - Discover what a long-term financial relationship can do for you. Visit https://firstrepublic.com/startup today to learn more.
(22:15) Mentoring the next generation of investors
(30:51) Linode - Apply to their Rise program for founder-led, early-stage startups and get 3 years of discounts at https://linode.com/twist.
(31:58) Sometimes incredible companies make the founder
(34:07) The greatest founders Doug has worked with
(46:30) Providing companies with a running start, but not doing too much
(53:10) Investing in China
(57:15) Entrepreneurship in Europe
(01:11:06) “Hope is not a plan. Let’s make a plan.
Check out Sequoia: https://www.sequoiacap.com
FOLLOW Doug Leone: https://www.linkedin.com/in/douglas-leone-a2714/
FOLLOW Jason: https://linktr.ee/calacanis
FOLLOW Molly: https://twitter.com/mollywood
The Tiger Global Memo: From Sequoia Capital to Benchmark and Thrive: The World's Best on the Rise of Tiger Global
Tiger Global are one of the most discussed venture firms on the planet. With a deal cadence and capital deployment speed that is unmatched, they have made their mark on the venture landscape like no other over the last 24 months. Today we are joined by leaders from Sequoia, Benchmark, Thrive Capital, General Atlantic, GGV and Aleph to discuss the rise of Tiger and how it impacts the venture ecosystem.
In Today's Episode on Tiger Global You Will Learn:
1.) Doug Leone: Sequoia Capital
Why we need to change the words when use in venture? Why we need to get rid of "the game"?
How does the rise of Tiger compare to the rise of prior entrants with the same approach?
Why does Doug believe that the craft of venture will persist despite these new entrants?
2.) Bill Gurley: Benchmark Capital
How does Bill analyse the change in late stage venture today?
What are the main drivers of the increased competition in late stage venture?
Why does Bill get concerned not by Tiger but how others respond to Tiger's model?
How does Bill analyse the entry of hedge funds and PE funds into traditional venture models?
3.) Michael Eisenberg: Aleph
How does Michael think about the "weaponisation of capital"?
What are the significant benefits for a fund of having more capital than their competitors?
How does this capital advantage change in boom and bust times?
4.) Anton Levy: General Atlantic
Why does Anton believe that funds are leveraging their assets more efficiently than ever?
How does Anton approach the mindset of AUM scaling without lowering returns?
Why does Anton never want to compete on price?
How does GA think about competing in a world of Tiger and hedge funds investing in tech?
5.) Hans Tung: GGV
Why did Hans always believe the model to look at moving forward was Tiger?
Why does Tiger's business model allow them structural and financial advantages over their competitors?
What does Hans make of the data network effects of Tiger with their strategy?
6.) Kareem Zaki: Thrive Capital
Why does Kareem think Tiger's approach makes absolute sense?
Why does Kareem believe so many in venture like to try and discredit the Tiger model?
How does Tiger's approach differ to Thrive's?
20VC: Sequoia's Doug Leone on What Has Been Instrumental To Scaling Sequoia Over Generations, How Sequoia Think About International Expansion and What They Learned From China and India & Why When You Lose Pre-Seed You Become Private Equity
Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more. As for Doug, he joined Sequoia over 33 years ago and has led investments in Nubank, Meraki, ServiceNow and TradeRepublic to name a few.
In Today's Episode with Doug Leone You Will Learn:
1.) How a 5PM Monday meeting with Don Valentine led to Doug joining Sequoia over 33 years ago? What did Don ask Doug in the meeting? What does Doug believe led Don to offer him his first role at Sequoia?
2.) The Leader: How did Doug change when he made the transition from a "COO" role to more of a "CEO" role with Sequoia? Doug has previously said, "Sequoia is a team, not a family". What does he mean by this? How do Doug and Sequoia do to give the team an unwavering sense of duty to the Sequoia brand? What does Doug believe Sequoia have done so well to allow them to move seamlessly from generation to generation?
3.) The Investor: Doug's first 3 investments all went on to successful IPOs, how did this impact his mindset at the time? What does Doug mean when he discusses "the abyss" he went through post this time? How does Doug advise others going through the abyss? What are the signs certain people will make it through vs not?
4.) The Landscape Today: How does Doug think about and react to newer entrants like Tiger and Softbank? How does Doug think about and assess his own price sensitivity today? How does Doug determine when to be disciplined vs when to pay up? Through what lens does Doug assess the compression of deployment cycles in venture today? Should we "play the game on the field"?
5.) The Expansion: In 2005, Sequoia expanded to China. Why was this the right time? What was the decision-making process for the Sequoia China team? Why does Doug believe, "when you lose pre-seed, you become private equity"? How does Doug react to the notion that success in venture is cyclical and compounds?
Item's Mentioned In Today's Episode with Doug Leone
Doug's Favourite Book: The Fountainhead: Ayn Rand, Antifragile: Things that Gain from Disorder
Sequoia Capital Part II (with Doug Leone)
The wait is over. Acquired returns with a very special Part II of the Sequoia Capital story, joined by the very best person in the world to help us tell it - Doug Leone. Since 1996, Doug has served as Sequoia’s Global Managing Partner, in charge of overseeing the firm’s incredible expansion from a single, $150m early-stage fund focused on Northern California to the multi-billion dollar global powerhouse it is today. Doug is incredibly candid and insightful about all that has gone into building the modern Sequoia: from winning Google and missing Facebook, to the enormous (and enormously successful) bet on decentralized expansion in China and India, to the firm’s “proudest moment” at the depth of the dot com bust. This episode is an absolute must-listen for anyone in the tech, startup and venture ecosystems today. Thank you to Doug and all of the Sequoia team for joining us to make it happen!
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Note:
You can listen to Part I of our Sequoia story, which dives deep into the history and background of the firm, here: https://www.acquired.fm/episodes/sequoia-capital-part-1
Sources:
https://www.brunswickgroup.com/sequoia-capital-doug-leone-silicon-valley-i11786/
https://www.sequoiacap.com/people/doug-leone/
https://www.sequoiacap.com/newsletter/2018-06-20-doug-leone
https://www.youtube.com/watch?v=5Er4QcNdjVU
https://www.linkedin.com/in/douglas-leone-a2714/
https://www.youtube.com/watch?v=4cl8X02Xd1I
https://www.youtube.com/watch?v=KrJgwKiEpaI
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