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Most venture capitalists have never actually built companies.
Tony Conrad did both.
In this episode, Mike sits down with Tony Conrad, Partner at True Ventures and one of the earliest investors behind companies like Blue Bottle Coffee, Sweetgreen, Madison Reed, Modern Animal, WordPress and more. Before venture capital, Tony spent a decade at Danone before leaving corporate life to build startups during the earliest days of Silicon Valley’s internet boom.
Tony shares what it was really like living through the dot-com crash, why he believes AI is creating another major market correction and the lessons founders keep ignoring when it comes to fundraising, valuations, and building sustainable companies.
The conversation goes deep into founder psychology, venture incentives, why most investors get founders wrong and how Tony evaluates companies before there’s even product-market fit.
He also breaks down:
- Why he instantly invested in Blue Bottle
- The danger of overheated seed valuations
- Why most founders choose the wrong investors
- The real role of storytelling in fundraising
- What separates iconic founders from everyone else
- Why “fast money” creates long-term pressure
- How AI is reshaping both enterprise and consumer investing
- Why he still believes consumer is massively underrated
You’ll learn:
✅ Why Tony left Danone for Silicon Valley startups
✅ What the dot-com crash taught him about AI today
✅ The founder traits most investors overlook
✅ Why inflated valuations hurt founders later
✅ How True Ventures thinks about ownership and returns
✅ Why Blue Bottle was an obvious bet for him
✅ The difference between scalable venture bets vs angel investing
✅ Why founder-investor alignment matters more than valuation
✅ How to know if you have the right investors around the table
✅ Why consumer investing always comes back
👉 If you’re a founder, operator, or investor trying to understand how great companies are actually built across multiple cycles, this episode is packed with hard-earned lessons.
Timestamps
00:00 Intro
01:00 Leaving Danone for Silicon Valley
04:00 Why tech felt more exciting than CPG
05:30 The early days of startup investing
08:00 Moving to San Francisco during the internet boom
10:00 Lessons from the dot-com crash
13:00 Is AI in a bubble right now?
15:00 How Tony joined True Ventures
17:00 Building startups while investing simultaneously
20:00 The burnout of being both founder and VC
22:00 Why Tony loves four-wall retail businesses
23:00 The Blue Bottle investment story
27:00 How True Ventures makes investment decisions
29:00 Why being a generalist investor matters
32:00 Angel investing vs venture investing
34:00 What “venture-scale” really means
35:00 The one mistake Tony hates making
36:00 How to identify the right founders
39:00 Why founders shouldn’t rush fundraising
41:00 The danger of inflated valuations
45:00 What founders should look for in investors
47:00 When founders should step aside as CEO
50:00 Balancing founder support with LP responsibility
51:00 Lessons from building About.me
55:00 Why digital identity still matters
56:00 Why consumer investing is underrated
58:00 AI infrastructure vs AI applications
01:00:00 Consumer AI opportunities Tony is excited about
01:02:00 Investing in competing companies
01:05:00 The problem with mega funds
01:07:00 Lessons from Slack & Stewart Butterfield
01:08:00 Favorite books & leadership lessons
01:11:00 AI, job displacement & optimism for the future
01:14:00 Final thoughts
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