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Dan Lewis

Co-founder & CEO, Stealth AI Startup · 1 appearance on the record.

computed by AI from the episodes · how this works → · full disclaimer →

founderexecutiveoperator@daniellewis ↗LinkedIn ↗

Dan Lewis is the co-founder and former CEO of Convoy, a digital freight marketplace that reached a $3.8 billion valuation before shutting down in 2023. Following Convoy's acquisition by Flexport, he served as a product executive at Microsoft before founding an AI stealth venture.

13statements → 2claims → 1claims resolved → 4/5average certainty → 1.62/5average debate potential → ≈4.5/5argument clarity, estimated → 5said about them ↓

1 supported 0 partly supported 0 contradicted 1 not checkable as stated how the 2 claims stand · each chip opens the sources

1 prediction · 1 assertion · 6 insights · 5 disclosures · every statement was checked. The prediction and assertion are the 2 claims: statements the public record can support or contradict. 1 is resolved, and 1 names no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Dan argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Dan Lewis: Truck driver smartphone adoption in 2014 enabled Convoy's model
“With Convoy, timing was crucial, and the reason it's working really well is on the trucking side, in 2014, approximately 2015, drivers started getting smartphones with a data plan and GPS. And, you know, most of the U.S.-based phone carriers started offering t…”
Dan Lewis Mar 23, 2018 ▶ 8:25 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy

How they sound: speaking style how? →

285 words/min while actually speaking · 2 um and uh per 1k words

No argument clarity score for Dan Lewis: no usable question→answer exchanges on raw tape (a fair score needs 8+). We do not score a sample that small. Roundtable and news formats yield far fewer direct exchanges than interviews. Their coarse estimate from 25 exchanges on the produced feed is ≈4.5/5, shown at half point precision because the sample is small and produced tape scores higher.

Measured by listening to 5,572 words across 1 episode, but every recording we have of Dan Lewis is the aired feed, and an editor cleaned that audio before release. Some of the hesitation was cut before we ever heard it, so read these as floors: the true rates are at least this high. These are measurements of speaking style, not scores. How it's measured →

How the interview went all their pushback → series average →

Across 1 rated episode:

host pushback ▾ 2/10
pushed back at the host 1/10
setup questions received 65%

Everything Dan Lewis said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Disclosure
Dan Lewis: Convoy rejected board advice to expand into port drayage
“I think at one point the board was pretty convinced we really needed to go into, you know, working with the ports, doing container dredge and things like that. And, you know, that was all part of us becoming more educated about this business. And just like me,…”
Dan Lewis Mar 23, 2018 ▶ 13:37 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Insight
Dan Lewis: Freight marketplaces require immediate multi-city scale unlike consumer apps
“The best comparison there is a lot of times when a consumer marketplace is forming, it can form in a neighborhood, right? You can have a service that forms within one specific neighborhood, food delivery service, or something, or you can have one that forms wi…”
Dan Lewis Mar 23, 2018 ▶ 15:35 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Insight
Dan Lewis: The best indicator of scaling is hiring your own replacement
“That is the best indicator as to whether someone's ready to scale with the company and step up and take on a bigger role and more responsibility is, are they able to step back and recognize that they need to hire someone to do their own job? Can they be comfor…”
Dan Lewis Mar 23, 2018 ▶ 24:40 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Insight
Dan Lewis: Core values must drive daily meetings, not just recruiting
“Having a set of core values that you don't just use to talk about the business to recruits, but they use every single day in meetings and in reviews and in hiring and these values, you kind of go back and back, you know, you go back to over and over again.”
Dan Lewis Mar 23, 2018 ▶ 4:44 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Disclosure
Dan Lewis: Convoy used famous founder investors to win traditional customers
“And so when we were able to get investors that had built significant companies to come be a part of Convoy, that lent a lot of credibility and trust to our customers where they could say, okay, the founder of Amazon or the person who, you know, created and dev…”
Dan Lewis Mar 23, 2018 ▶ 10:19 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Insight
Dan Lewis: Founders must own decisions rather than blindly following boards
“Take the decision and own the outcome of the decision. Your board is giving you advice. It probably sometimes feels like because everyone on the board is often more experienced than you or has had more success to date in their career, that what they say is wha…”
Dan Lewis Mar 23, 2018 ▶ 12:41 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Insight
Dan Lewis: Selling to traditional industries requires disrupting established workflows
“Trucking is a pretty traditional industry, and folks that work in the supply chain industry have been doing this for a while. We're not bringing them something they've never purchased before and saying, here's this thing you need. We're saying, you've been pur…”
Dan Lewis Mar 23, 2018 ▶ 18:33 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Insight
Dan Lewis: Building an experimental culture requires hiring from data-centric companies
“And so one of the ways you create a culture of experimentation is you hire a lot of People who have been part of organizations and companies that do a lot of experiments. And then that, that can be both the type of person from where they come, like the company…”
Dan Lewis Mar 23, 2018 ▶ 20:04 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Prediction Not checkable as stated
Dan Lewis predicted in 2018 that trucking would transform by 2023
“Logistics and trucking today are about where industries like retail, music, travel, et cetera, were a decade ago. A lot of early progress, but things are just starting to get interesting. I think that over the next five years, you're going to see incredible in…”
Dan Lewis Mar 23, 2018 ▶ 27:24 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Assertion Supported
Dan Lewis: Truck driver smartphone adoption in 2014 enabled Convoy's model
“With Convoy, timing was crucial, and the reason it's working really well is on the trucking side, in 2014, approximately 2015, drivers started getting smartphones with a data plan and GPS. And, you know, most of the U.S.-based phone carriers started offering t…”
Dan Lewis Mar 23, 2018 ▶ 8:25 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Disclosure
Dan Lewis: Convoy gamifies experiments by having employees vote on outcomes
“One thing we do that's fun, though, is when we do different types of experiments, especially ones that have more UI or more, we can frame them more clearly to the employees. We put them up on a wall in our office, and we'll have, like, the three treatments, or…”
Dan Lewis Mar 23, 2018 ▶ 21:25 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Disclosure
Dan Lewis evaluated multiple business models with Hadi and Ali Partovi
“And I spent a lot of time actually with Hadi Partovi and Ali Partovi exploring some of these ideas early, my co-founder, Grant Goodale. And then we kind of came up with the right business model in addition to, you know, four or five other ones that we looked a…”
Dan Lewis Mar 23, 2018 ▶ 4:03 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy
Disclosure
Dan Lewis says Amazon influenced Convoy's culture more than Google
“I think the one that certainly influenced me the most, primarily because I was doing it right before I started Convoy, was Amazon.”
Dan Lewis Mar 23, 2018 ▶ 4:33 20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfing & How To Determine Whether Someone is Scaling with the Organisation or Not with Daniel Lewis, Founder & CEO @ Convoy

The other half of the tape: Dan Lewis's own voice is left out of every number here. Other people bring the name up 5 times in 5 episodes on 20VC. every mention, with the transcript →

Who brings them up most Harry Stebbings 4Anu Hariharan 1

Every mention by year

tap a year for its mentions
002244201820192020episodesmentions
024201820192020episodes it came up in
000.5214201820192020episodesmentions per episode
2020 1 mention in 1 episode
2018 4 mentions in 4 episodes 1 per episode

Appearances (1)

EpisodeDateSpeaking time
20VC: How To Strategically Build The Right Investor Base, Why Startup Timing is Like Surfi Mar 23, 2018 20m
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