BILLIONS

Today on BILLIONS, I'm sitting down with Aaron Levie, the co-founder and CEO of Box, who has rapidly transitioned his enterprise platform from a pure SaaS model into a cutting-edge playground for autonomous AI agents.
Aaron has a masterclass view of the data infrastructure that legacy tech giants wish they controlled. In this conversation, we pull back the curtain on the high-stakes battle for sovereign AI.
We unpack the real fallout of the U.S. government's unprecedented export controls on Anthropic's frontier models, why data platforms like Snowflake are posting blockbuster quarters amidst the AI boom, and how specialized tools like Cursor show that the future of intelligence is multifaceted, not winner-take-all.
If you want to understand where the real economic value of applied AI resides over the next decade, this is the blueprint.
In this masterclass, we break down:
The Export-Control Precedent: Inside the unprecedented restriction of Anthropic's frontier model from non-US users and why Aaron calls it a brand-new moment in AI regulation.
The Safety-Rhetoric Boomerang: How AI safety messaging scared the government into a model-approval pipeline — and why some safety advocates may quietly prefer that outcome.
China's $50B Scenario: Why Aaron believes China can simply throw $50B at compute to stay in the race and why France, Japan, the UK, and Germany may be forced to build their own sovereign models.
The Multifaceted Intelligence Future: Why the AI market won't be "winner-take-all," and how Cursor's applied-layer harness (routing tasks across cheap and premium models) became the template.
Building for Machine Users: How Box adapted its file system MCP server, CLI, Markdown editing, HTML compatibility so agents and people work off the same data.
Why More Agents Make SaaS More Valuable: Why deploying 100x more agents than employees increases the value of the underlying CRM, ERP, and content systems instead of killing them.
The CS-Grad Dislocation: A grounded look at the shifting job market away from Big Tech layoffs and into AI startups and industries like life sciences and manufacturing.
TIMELINE :
00:00 – Turning Box from SaaS into an AI agent platform
03:00 – Sovereign AI: why countries will build their own models
05:51 – Can open and Chinese models catch up to the frontier?
08:51 – The chip embargo debate and Jensen Huang's argument
14:09 – AI safety, regulation, and government model approval
18:29 – Why AI won't be winner-take-all (the Cursor case study)
21:33 – How Box built a file system for AI agents
27:17 – Is SaaS dead? Why agents make software more valuable
30:48 – Will AI replace jobs? The truth about CS grads

Today on BILLIONS, I'm sitting down with Pete Maldonado, the visionary who took $6,000, one failed food venture behind him, and zero institutional backing and built a dominant food empire that's approaching $1 billion in revenue this year.
Pete and his co-founder Rashid bet everything on a category the entire industry assumed was dead: the gas-station meat stick.
For nearly ten years they bootstrapped taking less than $1M in primary capital prioritizing extreme operational focus and deleting complexity at every corner.
They stayed so maniacally disciplined that they only ever scaled one product format : meat sticksusing just 12 core recipes to capture market share from corporate giants.
But extreme efficiency comes with massive friction.
Pete opens up about the devastating reality of underestimating their explosive demand curve, which cost them 9 figures in lost revenue last year alone, the inside story of surviving an overnight COVID collapse with Trader Joe's, and why he chose to step down as CEO to hand over the keys to his co-founder.
In this masterclass, we break down:
The $6,000 Side Hustle Genesis: How a personal trainer used early Shopify tools and a $99 Photoshop Elements subscription to design a world-class brand from his desk.
The Rule of Deleting Complexity: Why going deep on a single SKU beats going wide, and how relentless simplicity early on became the reason they could scale at all.
The 9-Figure Forecasting Nightmare: The brutal operational pain of undershooting cultural shifts and cutting massive amounts of purchase orders when demand outpaces supply.
The Over-the-Register Museum Trap: How an unexpected plexiglass policy at Trader Joe's wiped out retail sales overnight during COVID—and the pivot that saved the team from layoffs.
The Hidden Weight of Personal Guarantees: Moving past bank-debt structures that put family homes on the line to engineer a 100% secondary private equity deal with Stride Consumer Partners.
Stepping Down at the Peak: Pete's candid psychological transition from active day-to-day CEO to hands-off Chairman to protect his family time and scale the company further.

TIMELINE :
00:00 – Building Chomps on $6,000: a $6,000 food brand from nothing
09:46 – Brand awareness vs. distribution: never hit a shelf before the customer knows you
11:53 – Riding the diet tribes: CrossFit, Paleo, Whole30, Keto, and now GLP-1
19:13 – The 2016 Trader Joe's inbound: staying methodical and rejecting advisor pressure to over-expand
28:05 – Forecasting demand and surviving COVID33:31 – The plexiglass "museum": surviving canceled COVID orders with zero layoffs
37:17 – Personal guarantees & the 100% secondary raise: de-risking the families
40:46 – Casting a wider net: breaking the bottom-of-funnel ROAS trap to unlock top-of-funnel scale
46:15 – Stepping down: from CEO to Chairman
REFERENCES
Rashid Ali 

Noah Kagan 

Tim Ferriss 

Liz Carter 

The Million Dollar Weekend 

Nutrisystem 

Jenny Craig

Trader Joe's

Whole Foods

Sprouts

Thrive Market

Jack Link's

Slim Jim

Stride Consumer Partners

Shopify

WordPress

Amazon 

Whole30 Approved 

CrossFit 

Paleo 

Keto 

GLP-1

On this episode of BILLIONS, I'm sitting down with Jason Wilk, four-time founder and CEO of Dave, the neobank built to take on the predatory overdraft fees that quietly bleed billions a year from the Americans who can least afford them.
Jason's story is one of the wildest comebacks in fintech. After going public via SPAC in January 2022, Dave hit a $5 billion valuation, then the macro turned.
Rates spiked, growth capital dried up, and within nine months the stock had collapsed 98%, dragging the company's market cap down to roughly $50 million, less than the cash sitting on its own balance sheet.Most teams would have panicked, slashed headcount, or sold cheap.
Jason did the opposite: he froze hiring, refused layoffs, killed every non-core product, and put the entire company behind one number, unit economics.
Today Dave is back to a nearly $4 billion market cap, with 2026 guidance of over $700M in revenue and over $300M in EBITDA, a ~$400M earnings swing in just a few years.
In this masterclass, we break down:
The $75 microloan bet : how Dave used cash-flow data instead of FICO to underwrite the smallest loan in the country, importing a model that worked in India and Africa but no one had cracked in the US.
120 meetings for a Series A : why traditional VCs had never even heard of overdraft fees, and what it took to finally get the check.
Surviving a 98% wipeout : the operational playbook Jason ran when growth capital ground to a halt and raising more was off the table.
Making millionaires at the bottom : how a Performance Stock Unit structure turned the crash into the biggest wealth-creation event in the company's history.
"VC money is just very high-APR debt" : why Jason wishes he'd taken his $10M Series A as venture debt and kept the equity.
Eating other people's margin : Dave's new credit card and multi-product roadmap, aimed at the $100B+ a year Americans pay in credit card APRs and late fees.
TIMELINE :
00:00 – Why he declared war on the $34 overdraft fee
01:55 – The $75 microloan that ignores your credit score
04:26 – 120 investor meetings to close the Series A
09:48 – Going public via SPAC at a $5B valuation
11:15 – How the stock crashed 98% in 9 months
16:19 – Making employees millionaires at rock bottom
19:38 – From burning $100M to $300M in EBITDA
23:17 – Why VC money is worse than a loan shark
27:00 – The new credit card attacking a $100B market
43:29 – Running a $4B company with 300 people

REFERENCES :
Jason Wilk

SV Angel 

Ron Conway

Paul Graham

GoBuyside / « Gocleff » 

Dave 

Plaid

Acorns 

BankSimple 

Norwest Venture Partners 

Tiger Global 

Y Combinator

On this episode of BILLIONS, I'm sitting down with Peter Singlehurst, who built the private companies team from scratch at legendary investment firm Baillie Gifford, deploying billions into more than 100 of the most important private companies on the planet.
Peter operates on a timeline that makes typical venture capitalists look shortsighted. From backing Tesla in 2013 at a $3B market cap to entering SpaceX at a $30B valuation, his strategy completely bypasses the short-term noise of quarterly earnings.
In this masterclass, he breaks down why optimizing for the highest possible price at an IPO is a lethal mistake, the massive arbitrage hidden within the world's most misunderstood tech giant (ByteDance), and the raw post-mortem of their highest-profile mistake: Northvolt.
We break down:
The Philosophy Swerve: How a philosophy graduate skipped a PhD to build a multi-billion dollar growth engine and why Baillie Gifford deliberately hires people with no finance background.
The Death of the IPO Monopoly: Why the world's most valuable hyper-growth companies no longer need public exchanges to unlock liquidity.
Debt Kills, Dilution Doesn't: Peter's contrarian warning to scaling founders on why leverage is a ticking time bomb for pre-profitable businesses.
The ByteDance Arbitrage: The inside story of buying shares at ~4x free cash flow while Western investors ran away.
The Northvolt Post-Mortem: A transparent breakdown of their highest-profile mistake and how to spot a venture-stage asset masquerading as a growth-stage giant.
Disrupting the 2-and-20 Norm: How Baillie Gifford structures an ultra-LP-friendly 1-and-10 fee model charged on invested capital, not committed capital.
TIMELINE :
00:00 – "You get the shareholders you deserve": the long-term underwriting mindset
00:53 – From philosophy to growth equity: why Baillie Gifford avoids finance backgrounds
05:44 – Entry mechanics: Tesla's $3B public entry vs SpaceX's $30B private scale
08:23 – The leverage trap: why a little dilution never killed a business, but debt does
13:50 – Democratizing elite assets: how the Schiehallion Fund opens up Stripe, SpaceX & Databricks to everyday savers
23:15 – Designing the ideal IPO: why chasing the highest possible price destroys public-market trust
30:07 – The founder risk matrix: Bezos' 1997 shareholder letter & Musk's "bet the house" blueprint
35:30 – The ByteDance arbitrage: buying shares at ~4x free cash flow
52:47 – Flipping the venture fee model: the LP-friendly 1-and-10 on invested capital
56:09 – The Northvolt post-mortem: growth equity risk vs venture equity risk

REFERENCES
Elon Musk 

Jeff Bezos 

Jeff Bezos’s letter to his shareholders in 1997

Warren Buffett 

Larry Ashbrook

Hendrick Borginon 

Baillie Gifford 

Tesla 

SpaceX 

ByteDance 

Amazon 

Alibaba 

Anduril 

Bending Spoons

Airbnb

Spotify 

Stripe

Databricks

Affirm

Wise

Tempus

Klarna 

Figma

Northvolt

Uber

Lyft

Meta (Facebook)

On this episode of BILLIONS, I'm sitting down with elite finance operator Martino Cadoni, current CFO of DeepL (one of Europe's leading AI companies) and the veteran strategist behind one of Central Europe's biggest banking IPOs.
Martino cut his teeth in corporate America's legendary "CFO factory" the grueling General Electric leadership program, working relentless 996 schedules to solve high-stakes financial fires across the globe.
From being flown to Budapest on a day's notice to re-evaluate multi-million dollar reserves in two weeks during a currency crisis, to managing capital and balance-sheet strategy as deputy CFO at HSBC, Martino knows exactly what it takes to build institutional readiness.In this masterclass, he pulls back the curtain on private vs. public markets, exposing the lethal structural mistakes tech unicorns make during down rounds and explaining exactly how legacy banking giants accidentally funded their own demise.
In this masterclass, we break down:
The GE CFO Factory: Inside the intense 996 operational rotation program that builds high-agency, first-principles problem solvers.
The "Zombie Corn" Trap: Why raising capital at massive valuations with high preferred share thresholds completely paralyzes tech startups when the market turns.
The Balance Sheet Obsession: Why optimizing accounts payable, invoice due dates, and basic payment timing yields instant cash flow wins that most tech companies completely step over.
The AI Billing Paradigm Shift: Navigating the massive industry uncertainty around revenue models—from traditional per-seat subscriptions to usage and outcome-based billing.
How Traditional Banking Lost: Why legacy financial institutions wasted billions on stock buybacks and short-term dividends instead of innovating, allowing Revolut and Nubank to ruthlessly strip away their market share.

TIMELINE :
00:00 – Finance as an Accelerator: The core value-creation thesis + who Martino is (from a $749M banking IPO to DeepL).
01:26 – The GE "CFO Factory": Rotations, the 996 schedule, the Budapest currency emergency, and the Toyota/agile principles behind high-agency finance.
10:34 – The Balance Sheet Obsession: Why tech over-indexes on the P&L, and the easy cash wins in accounts payable, invoice timing, and FX.
17:48 – Public Markets, SOX & the Cost of Capital: Building precise guidance, how interest-rate cycles dictate fintech lending, and Revolut's revenue diversification.
27:49 – The "Zombie Corn" Trap: How high preferred-share thresholds freeze startups when the market turns and the common-share advantage.
35:12 – Down Rounds & Cap Table Management: Pitching fresh investors a path to upside, and why a concentrated cap table lets you manage LPs one-on-one.
41:26 – Why DeepL & the AI Billing Shift: Joining Europe's AI race, and the industry struggle to move from per-seat to usage and outcome-based pricing.
50:13 – Defensibility & the Short-Term Trap: Avoiding FOMO, building embedded moats, and how legacy banks burned billions on buybacks while Revolut and Nubank ate their lunch.

REFERENCES
Thierry Pieton

Kazuma Shipchandler

John Elkann 

Jarek Kutylowski

Matt Cohler 

Danny Rimer

General Electric (GE) 

Converteam 

Moneta Money Bank

Klarna 

DeepL 

Revolut 

Benchmark

Index Ventures

IVP

Iconic

B2Venture

GIC

ATomico

Ontario Teachers' Pension Plan