Spike Lipkin

Chief AI Officer, WTW · 1 appearance on the record.

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

founderexecutiveoperatorinvestorLinkedIn ↗newfront.com ↗

Spike Lipkin co-founded and served as CEO of Newfront, a commercial insurance brokerage that grew to unicorn status before being acquired by WTW. Following the acquisition, he became WTW's Chief AI Officer, having previously worked at Opendoor and Blackstone.

16statements → 6claims → 0claims resolved → 3.75/5average certainty → 1.69/5average debate potential → ≈4.5/5argument clarity, estimated → 8said about them ↓

6 not checkable as stated how the 6 claims stand · each chip opens the sources

1 prediction · 5 assertions · 1 opinion · 6 insights · 3 disclosures · every statement was checked. The prediction and assertions are the 6 claims: statements the public record can support or contradict. 0 are resolved, and 6 name 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 Spike argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

How they sound: speaking style how? →

264 words/min while actually speaking · 0 um and uh per 1k words

No argument clarity score for Spike Lipkin: 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 24 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 3,196 words across 1 episode, but every recording we have of Spike Lipkin 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 →

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

Prediction Not checkable as stated
Spike Lipkin predicts the next tech era will be defined by services
“If the last phase of technology was characterized by companies selling technology, I think the next phase will be characterized by technology companies selling services.”
Spike Lipkin Oct 16, 2020 ▶ 20:45 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Assertion Not checkable as stated
Newfront CEO Spike Lipkin met with only one external investor in 2019
“Last year in 2019, I think I met with one investor who's not on our cap table right now.”
Spike Lipkin Oct 16, 2020 ▶ 16:04 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Assertion Not checkable as stated
Newfront accepted Kevin Hartz's investment offer despite it being 30% lower
“When Kevin invested, we had some other offers that were materially higher than his. I think his was 30% lower than the next offer.”
Spike Lipkin Oct 16, 2020 ▶ 19:12 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Insight
Startups should ignore secondary problems because scaling unlocks resources
“The nature of startups is that if they start working, you unlock resources and talent, and so, so many problems that seem hard today get easier over time, and I think Opendoor was kind of ruthlessly focused on solving the most important problems at the time, k…”
Spike Lipkin Oct 16, 2020 ▶ 4:57 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Insight
Lipkin: Founders should solve zero-to-one problems before delegating them
“And so we try not to delegate zero to one problems. We try to solve those ourselves and then very quickly find capable people to delegate those things to.”
Spike Lipkin Oct 16, 2020 ▶ 5:48 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Insight
Exposing operational flaws to candidates attracts top executive operators
“What we've found is that if we go talk to an incredible operator and expose all the things that are broken in our business, but also show the things that are working. What gets them excited is the fact that they probably can solve the things that are broken an…”
Spike Lipkin Oct 16, 2020 ▶ 9:01 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Insight
Lipkin: Startups shouldn't reinvent the wheel on building operations organizations
“We think a lot about the risks we're taking as a business, and we want to innovate on client experience and broker experience. We didn't want to innovate on creating a best-in-class ops org. We felt like this was not an area where we needed to reinvent the whe…”
Spike Lipkin Oct 16, 2020 ▶ 10:18 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Insight
Lipkin: Investors add top value by helping founders isolate key business priorities
“One of the advantages investors have is this bird's eye view where they can help founders identify, you know, the two or three most crucial elements of the business that need to be addressed.”
Spike Lipkin Oct 16, 2020 ▶ 18:41 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Insight
Lipkin: Tech-Enabled Service Startups Can Achieve Differentiated Margins in Huge Markets
“In our experience, if you leverage technology to provide a differentiated client experience, you often can also leverage technology to provide differentiated margins. So I think it may not be the world of 99% gross margins that Google experience, but it will b…”
Spike Lipkin Oct 16, 2020 ▶ 21:03 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Opinion
Lipkin: Commercial insurance is vital to the economy but understood by no one
“Insurance was crazy. Crucial to our society, crucial to our economy, crucial to entrepreneurship, and really understood by no one.”
Spike Lipkin Oct 16, 2020 ▶ 3:52 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Disclosure
Newfront mapped executive energy levels to divide leadership responsibilities
“We did this exercise early on where a lot of the execs on my team wrote down a list of things that gave them energy, and that they loved doing, and felt like they were very good at, and things that took energy from them, and they Didn't enjoy doing and didn't …”
Spike Lipkin Oct 16, 2020 ▶ 7:00 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Disclosure
Newfront scaled customer service without ticketing systems or SLAs
“And so we were running a scaled customer service org without a ticketing system, for instance, we didn't have SLAs in place.”
Spike Lipkin Oct 16, 2020 ▶ 11:29 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Assertion Not checkable as stated
Spike Lipkin: Newfront's last three funding rounds were preemptive insider-led rounds
“We've been lucky that our last three funding rounds have been preemptive, and mostly it's been insiders wanting to lead subsequent rounds”
Spike Lipkin Oct 16, 2020 ▶ 15:42 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Assertion Not checkable as stated
Spike Lipkin: Newfront met weekly with Kevin Hartz for years during scaling
“We were lucky enough to work with Kevin Hartz and met with him once a week for a number of years to think through some of the common challenges of scaling.”
Spike Lipkin Oct 16, 2020 ▶ 16:36 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Disclosure
Spike Lipkin: Michael Ovitz Is an Angel Investor and Cultural Advisor at Newfront
“The other one is Michael Ovitz. He built CAA, which Is the largest talent agency in Hollywood. We've learned a huge amount from him about how to build our culture and team at Newfront.”
Spike Lipkin Oct 16, 2020 ▶ 20:29 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Assertion Not checkable as stated
Lipkin: Opendoor leadership focused heavily on recruiting early on
“When I looked at how Eric, Ryan, JD, Keith spent time, it was very much focused on recruiting incredible people.”
Spike Lipkin Oct 16, 2020 ▶ 4:37 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance

The other half of the tape: Spike Lipkin's own voice is left out of every number here. Other people bring the name up 6 times in 2 episodes on 20VC. 2 statements on the record name them. every mention, with the transcript →

Who brings them up most Harry Stebbings 6

Statements about Spike Lipkin, by other people (2)

Assertion Supported
Stebbings: Spike Lipkin raised over $100M for Newfront
“To date, Spike has raised over a hundred million dollars with Newfront for Some of the best in the business, including Founders Fund, Meritech, and of course, the newly founded TwentyVC Fund.”
Harry Stebbings Oct 16, 2020 ▶ 0:24 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance
Assertion Supported
Stebbings: Spike Lipkin helped scale Opendoor to a $5B+ enterprise value
“Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from five people to an enterprise value of over five billion dollars today.”
Harry Stebbings Oct 16, 2020 ▶ 0:34 20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors When Not Raising & The Most Important Non-Obvious Role of the CEO with Spike Lipkin, Founder & CEO @ Newfront Insurance

Every mention by year

Appearances (1)

EpisodeDateSpeaking time
20VC: How To Determine The Risks To Take vs To Pass On, Should Founders Meet Investors Whe Oct 16, 2020 12m
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