Sign up to save your podcasts
Or
Share Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Share to email
Share to Facebook
Share to X
Share to email
Share to Facebook
Share to X
Or
Doug Leone - Lessons from a Titan - [Invest Like the Best, CLASSICS]
Invest Like the Best
Key Takeaways
- Identify and invest in outliers: The best venture capital investors recognize outlier potential when they see it and have a curiosity to discover what makes the outlier tick and WHY they tick that way
- On being a VC or a founder: Inherent builders should be in the field – they should be building companies, not coaching other builders
- Debug problems as far upstream as possible; take the rocks out of the river so the water can flow as fast as possible
- Black magic is reserved for founders; every other area of the company-building process is mere mortal stuff
- Stewardship over ownership: The goal is to leave your creation in a better place for the next generation
- It is okay to choose the parallel tracked path of banking or consulting, and it is okay to take risks, but it is not okay to do one and spend your life thinking you did the other
- The most common mistake that investors make is doing something contrary to the best interests of the founder
- Traits of the best investment memos:
- (1) Clearly state the one or two strongest reasons to invest
- (2) Two to three pages max
- (3) Present clear data from the opposing side
- (4) argue why the investment should happen despite the opposing data
- Success starts at the foundational layer: Great culture is downstream of getting the foundation right and fostering internal belief, which is all a firm needs to be successful
- Performance is the cultural component that matters most
Read the full notes @ podcastnotes.org
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.
-----
This episode is brought to you by Passthrough. Passthrough streamlines subscription documents, KYC, and AML compliance, so you can focus on running your fund, not managing paperwork. New SEC Update 31 CFR hits investment firms in under a year, and managers are getting ready for it now. If you think basic OFAC screening is enough, think again.
You'll need continuous monitoring of your investors and all their beneficial owners across multiple watchlists, plus a comprehensive anti money laundering program. Passthrough has already processed 50,000 LPs and built the complete solution. Don't risk SEC deficiency letters, fines, or regulatory enforcement. Visit passthrough.com to get compliant now.
-----
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
View all episodes
By Podcast NotesInvest Like the Best
Key Takeaways
- Identify and invest in outliers: The best venture capital investors recognize outlier potential when they see it and have a curiosity to discover what makes the outlier tick and WHY they tick that way
- On being a VC or a founder: Inherent builders should be in the field – they should be building companies, not coaching other builders
- Debug problems as far upstream as possible; take the rocks out of the river so the water can flow as fast as possible
- Black magic is reserved for founders; every other area of the company-building process is mere mortal stuff
- Stewardship over ownership: The goal is to leave your creation in a better place for the next generation
- It is okay to choose the parallel tracked path of banking or consulting, and it is okay to take risks, but it is not okay to do one and spend your life thinking you did the other
- The most common mistake that investors make is doing something contrary to the best interests of the founder
- Traits of the best investment memos:
- (1) Clearly state the one or two strongest reasons to invest
- (2) Two to three pages max
- (3) Present clear data from the opposing side
- (4) argue why the investment should happen despite the opposing data
- Success starts at the foundational layer: Great culture is downstream of getting the foundation right and fostering internal belief, which is all a firm needs to be successful
- Performance is the cultural component that matters most
Read the full notes @ podcastnotes.org
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.
-----
This episode is brought to you by Passthrough. Passthrough streamlines subscription documents, KYC, and AML compliance, so you can focus on running your fund, not managing paperwork. New SEC Update 31 CFR hits investment firms in under a year, and managers are getting ready for it now. If you think basic OFAC screening is enough, think again.
You'll need continuous monitoring of your investors and all their beneficial owners across multiple watchlists, plus a comprehensive anti money laundering program. Passthrough has already processed 50,000 LPs and built the complete solution. Don't risk SEC deficiency letters, fines, or regulatory enforcement. Visit passthrough.com to get compliant now.
-----
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
More shows like Podcast Notes Playlist: Startup
View all
The Joe Rogan Experience
225,839 Listeners
Seth Godin's Startup School
424 Listeners
The Diary Of A CEO with Steven Bartlett
7,070 Listeners
Modern Wisdom
3,758 Listeners
All-In with Chamath, Jason, Sacks & Friedberg
9,261 Listeners
Boardroom with Rich Kleiman
611 Listeners
Tetragrammaton with Rick Rubin
1,018 Listeners