Mar 7, 2022 · 52m · capital-allocators
Annie Lamont – A Lifetime in Venture, Venture is Eating the Investment World 9 (Capital Allocators, EP. 238)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of Capital Allocators, host Ted Seides interviews Oak HC/FT Co-Founder Annie Lamont, exploring her 40-year venture capital career, specialized investment framework in healthcare and fintech, and strategies for navigating market cycles and building enduring platform companies.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Ted holds 26.5% of the talking time here. How this is scored →
Ted as informed peer 4.8 Guest teaching 5.5 Guest disagreement 1.6 Ted pushing back 1.8
speaking balance: gold is Ted, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 25:30 Blunt rejection of third-party consulting diligence
Annie forcefully rejects the standard private equity reliance on Bain or McKinsey, insisting that true venture domain specialists must possess firsthand operational knowledge.
Hardest push from Ted ▶ 42:01 Ted presses on the risk of size eroding venture performanceTed directly confronts the classic venture paradox of whether growing fund assets dilutes returns and forces firms into indexing the market.
Biggest teaching moment ▶ 14:44 Annie explains the structural failure of early biotech investingAnnie educates Ted on the market reality of the early 2000s, explaining why thousands of public biotech companies had only five approved drugs and why Oak redirected capital into tech-enabled healthcare.
Ted holds their own ▶ 46:32 Ted challenges venture platform expansion as an unsustainable arms raceTed articulates the operational pitfalls of firms building sprawling global footprints and specialized support teams.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Ted as informed peer | Guest teaching | Guest disagreement | Ted pushing back | Why |
|---|---|---|---|---|---|---|
| Annie Lamont's Early Career and 1980s Venture Foundations | 4 | 5 | 1 | 1 | Ted prompts Annie to recount the nascent venture ecosystem of the 1980s and the structural differences between East Coast and West Coast investing. Annie shares historical color on taking Apple and Genentech public, setting a collaborative and reflective tone. | |
| The Primacy of CEO Quality and Team Building | 5 | 6 | 2 | 2 | Ted probes on how Annie assesses CEO quality and manages strategic market pivots across tech bubbles. Annie explains the discipline of stepping back from dry sectors like early biotech to pioneer healthcare software and payments. | |
| The Genesis and Spin-Out of Oak HC/FT | 5 | 5 | 1 | 2 | Ted asks about the mechanics and branding decisions behind spinning out Oak HC/FT while the legacy partnership phased out. Annie outlines the cultural imperative to build a dedicated value-add platform around talent and operators. | |
| Investment Focus and Intersection of Healthcare & FinTech | 5 | 6 | 2 | 2 | Ted inquires into sourcing pipelines and how early-stage trends inform growth investing. Annie explains why avoiding binary FDA risks while targeting the regulated convergence of fintech and healthcare generates proprietary deal flow. | |
| Diligence Execution and Operator Value Creation | 4 | 5 | 1 | 1 | Ted asks how Oak HC/FT conducts due diligence and deploys operational talent. Annie dismisses third-party consulting firms, asserting that decades of deep domain knowledge allow them to complete internal customer diligence directly. | |
| Valuation Discipline and Market Reset in Tech Investing | 5 | 6 | 2 | 2 | Ted examines how surging capital inflows have affected deal terms and valuations. Annie clarifies that while entry prices inflated, discipline shifts to assessing long-term exit durability amid macro public market pullbacks. | |
| Healthcare Innovation: Pay-Vider Models and Workflow Automation | 5 | 6 | 2 | 1 | Ted asks about core emerging themes in healthcare delivery. Annie breaks down the mechanics of the pay-vider model where providers take on capitation risk, alongside the acute post-pandemic demand for administrative automation. | |
| Virtual Care, Home-Based Medicine, and Caregiver Support | 4 | 5 | 1 | 1 | Ted asks about specific business models capitalizing on virtualization. Annie highlights home-based acute care and platforms that empower low-wage caregivers to reduce expensive institutional hospitalizations. | |
| FinTech Transformation and Digital Asset Infrastructure | 5 | 6 | 2 | 2 | Ted asks about Oak HC/FT's perspective on crypto and decentralized finance. Annie distinguishes between speculative token trading and enterprise digital asset infrastructure like Paxos. | |
| Fund Sizing, Brand Moats, and Market Share Dynamics | 6 | 6 | 2 | 3 | Ted challenges whether scaling fund sizes compromises returns or creates an index-like approach. Annie defends their concentrated fund sizing by pointing to inflated round sizes and the necessity of brand market share to win competitive deals. | |
| Cycle Navigation, Inorganic Growth, and Global Footprint | 6 | 5 | 2 | 3 | Ted asks if geographic expansion and platform additions risk triggering a venture arms race. Annie counters that maintaining a small, partner-heavy model with high liquidity turnover prevents overexpansion. | |
| Public Policy Insights as First Lady of Connecticut | 4 | 5 | 1 | 1 | Ted asks Annie about balancing her investing role with public service as First Lady of Connecticut. Annie explains how understanding state-level policy complements healthcare and fintech investing while fostering local entrepreneurship. |
Statements from this episode (27)
Hambrecht & Quist took Genentech and Apple public within three months
“And the first three months I was there, we took Genentech Public. We took Apple Public. I carried Steve Jobs bags on the Apple IPO Roadshow, and I was just exposed to the two of the most amazing entrepreneurs ever, and I fell in love.”
Lamont: There was only one public software company in 1983
“I wasn't that interested in investing in disk drive companies, and there was only one public software company at that point.”
Lamont: Being outside Silicon Valley protected Oak from tech groupthink
“I actually loved being outside of Silicon Valley because I think it over my career has made us think differently. We aren't stuck in group think and have been invested all over the country and now globally.”
Lamont: Market Vision failed against Bloomberg due to focus on hardware
“Well, I think, you know, it was an entrepreneur that became obsessed with the hardware and the graphics and not the software and the business model, and Bloomberg was so brilliant around the business model and obviously the software.”
Lamont: Google and Amazon wouldn't exist without 1990s internet mania
“If we hadn't had a mania, we wouldn't have funded things like Google and Amazon, some of the great companies of today.”
Lamont: By 2000 there were 3,000 public biotech companies and 5 approved products
“That there were 3000 public biotech companies, and only five approved products.”
Lamont: Oak Investment Partners agreed to wind down and dissolve
“But the existing entity, Oak Investment Partners, wasn't going to exist any longer. That entity, we all agreed, was going to die. We were going to roll off all the companies, and we were the surviving new entity, essentially, Oak HCFT, so you could call us Oak…”
Oak HC/FT refuses to invest directly in FDA-risk biotech
“In terms of directly investing into biotech and life sciences companies that take FDA risk, we won't do that.”
Lamont: One-third of Oak HC/FT deals sit at the healthcare-fintech intersection
“Fintech and payments is really embedded in every industry, and it's one of the reasons there was incredible conversions between healthcare and fintech, two highly regulated industries, but a third of what we do is the overlap between these two sectors.”
Oak HC/FT rejects cold-calling sourcing models used by TA and Insight
“We don't cold call. We're not like a TA or an insight, have a bank of kids that are, they're trying to find deals. Just not the way it works.”
Lamont: Five-year-old growth companies are now frequently disrupted by startups
“1015 years ago, a growth company was very unlikely to be dislocated by a new company. A five-year-old company being dislocated by a new company, probably not happening. Now happens all the time.”
Lamont: Single-product startups will be forced to sell into platform companies
“And with the public markets declining and more challenges probably in the private market in terms of raising money, you're going to see companies that are really products and not platforms be sold. And be incorporated into these platform companies that we hope…”
Oak HC/FT never hires external consultants like McKinsey for due diligence
“And then otherwise, we don't hire McKinsey. We don't hire Bain. We never hire a consultant.”
Oak HC/FT invested in Paxos at $2B and quickly saw 2x offers
“We just invested in a company, Paxos, a couple months ago, two billion dollar valuation. We're already getting offers at more than twice that for that company.”
Lamont: Having Doctors Bear Long-Term Financial Risk Drives Highest Healthcare Impact
“This is truly what should happen across America at every level. I was like, you really should have doctors at risk. For managing patients over the long term. That's what's going to have the most impact.”
Lamont: Severe Staffing Shortages Are Forcing Healthcare Systems to Adopt Automation
“We found that whether it be a payer or providers, hospital systems, they really didn't care three years ago about efficiency automation. They cared about revenue enhancement, but they really didn't care about efficiency, and they threw staff and bodies at ever…”
Lamont: Automation, robotics, and sensors will radically transform home care
“The automation, robotics, sensors just the care platforms about managing caregivers that are managing individuals in their home is going to be dramatically different, and so we're seeing much more investment going into home care and virtualization.”
Lamont: Dispatch provides in-home ER services and dramatically cuts care costs
“Dispatch is actually providing, they have cars that literally provide ER and hospital-based services in your home. They come to your house, and it dramatically lowers the cost of care.”
Lamont: Oak HC/FT invests in digital asset infrastructure, not crypto tokens
“On the crypto side, we haven't been investing in it As a currency. We haven't been investing in crypto per se, but we invest in digital asset infrastructure. So Paxos is digital asset infrastructure.”
Lamont: Paxos provides white-label infrastructure that enables any entity to be Coinbase
“Pax is effectively makes everybody Coinbase. They've got the fully regulated white labeled infrastructure, so any entity can be Coinbase.”
Lamont: Female VC and CEO Representation Will Rise Concurrently
“You're going to see more female CEOs at the same time you're seeing more VCs, and it's happening.”
Lamont: Multi-stage venture firms have an advantage over standalone seed funds
“And even I think seed funds are having trouble because firms that can do seed startup series A, B, C, and promise to be there with the entrepreneur all the way along, have an advantage against an even a early stage seed fund.”
Oak HC/FT companies accounted for 30% of $100M+ sector rounds in 2021
“I mean, we were, last year, we were, 30% of the rounds that were done, over a hundred million in our sectors, were OKCFT companies. And that is a pretty powerful stat, and those were all over a billion dollar rounds, in terms of valuation.”
Lamont: Oak HC/FT restricts fund portfolios to 20 to 25 companies
“I think we have kept every fund is about 20 to 25 companies, so that's been an important stat.”
Lamont: Series B and C round sizes have tripled over five years
“Well, I think the industry solved it for us because the size of a Series B and C is three times what it was five years ago.”