Dec 18, 2017 · 39m · how-i-built-this
LearnVest: Alexa von Tobel
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In this episode of How I Built This, host Guy Raz interviews entrepreneur Alexa von Tobel, tracing how childhood adversity and widespread American financial illiteracy drove her to drop out of Harvard Business School and build LearnVest into a $250 million fintech platform.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 32.2% of the talking time here. How this is scored →
Guy as informed peer 5.1 Guest teaching 3.6 Guest disagreement 1.3 Guy pushing back 1.8
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:24 Rejecting the competitor label
Alexa gently but firmly rejects Raz's suggestion that she is driven by beating competitors, clearly categorizing herself as an internal achiever instead.
Hardest push from Guy ▶ 15:36 Pushing on leaving Harvard during a crisisRaz presses Alexa on why a rule-following, straight-A Harvard student would willingly abandon stability to launch a venture during a financial collapse.
Biggest teaching moment ▶ 24:35 Explaining the cost structure of financial plansAlexa breaks down the economics of traditional advisory firms versus her automated product, educating the listener and host on market pricing.
Guy holds their own ▶ 0:37 Raz outlining macroeconomic financial statsRaz demonstrates strong subject matter mastery by reciting nationwide statistics on median retirement savings, household credit card debt, and financial literacy deficits.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Growing Up in a Science-Oriented Household | 4 | 2 | 1 | 1 | Guy Raz sets up background context about von Tobel's upbringing in a medical and scientific household. Alexa elaborates cooperatively on early childhood memories and early exposure to financial discipline. | |
| The Loss of Her Father and Life's Fragility | 4 | 2 | 0 | 0 | Raz asks compassionate, reflective questions about the traumatic loss of Alexa's father. The tone is deeply emotional and entirely cooperative. | |
| The Spark for LearnVest: Household Finances in Crisis | 5 | 3 | 1 | 1 | Raz points out the practical financial strain when a key earner passes away. Alexa details how seeing her mother navigate the complex finances inspired the mission behind LearnVest. | |
| Early Entrepreneurial Drive and Starting at Morgan Stanley | 5 | 4 | 2 | 2 | Raz asks why someone in their early twenties would focus on financial planning rather than sexier topics. Alexa explains the widespread ignorance and anxiety around personal finance among young professionals. | |
| Dropping Out of Harvard During the 2008 Financial Crash | 5 | 4 | 2 | 3 | Raz probes Alexa's decision to drop out of Harvard Business School right as the 2008 financial crisis hit, noting she does not seem like a reckless risk-taker. Alexa counters with psychological insights on regret and seizing urgent opportunity. | |
| Bootstrapping in New York and the First Hire | 5 | 3 | 1 | 2 | Raz explores the economics of early bootstrapping with only $75,000 in savings in New York City. Alexa describes the intense hustle, phantom equity, and recruiting her first intern in a Starbucks. | |
| Raising Seed Capital in a Turbulent Economy | 6 | 4 | 2 | 3 | Raz questions how she successfully pitched and closed angel investors during the peak of the 2008-2009 economic meltdown. Alexa highlights her deep preparation with a 75-page business plan and relentless follow-ups. | |
| Launching LearnVest, Rapid Growth, and Series A | 6 | 4 | 1 | 2 | Raz probes the operational model and whether LearnVest relied on advisors or algorithmic software. Alexa explains the hybrid software model designed as TurboTax for financial planning. | |
| Scaling the Vision: Achiever Mindset and Mass Market Appeal | 5 | 5 | 2 | 2 | Raz asks whether Alexa is driven by competition and wanting to beat rivals. Alexa clarifies and reframes her personality type, drawing a sharp distinction between achievers and competitors. | |
| Northwestern Mutual Acquisition and Full-Circle Reflection | 6 | 4 | 1 | 2 | Raz brings up the quarter-billion dollar acquisition by Northwestern Mutual and connects it back to her family's early vulnerability. Alexa shares the full-circle realization that a Northwestern Mutual policy had saved her family at 14. | |
| Life Perspective, Facing Fear, and What Lies Ahead | 6 | 5 | 2 | 2 | Raz asks his signature question attributing success to luck versus skill. Alexa dismisses both pure luck and her own intelligence, crediting team execution and perspective gained from childhood trauma. | |
| How You Built That: Dylan Hill and Gamers Gift | 4 | 3 | 0 | 1 | Raz interviews Dylan Hill in the 'How You Built That' segment about creating Gamers Gift. The dialogue is completely supportive and narrative-focused. |
Statements from this episode (14)
Von Tobel: No Personal Financial Planning Classes Existed in College
“When I went to college, and I started getting, you know, studying things I'm interested in, I ended up literally, like, thinking to myself, I just want to take, like, some financial planning classes. Like, how many credit cards should I have? And, you know, ho…”
LearnVest Originated as a 75-Page Morgan Stanley Side Project
“I put together the 75 page-ish business plan that nobody read, but it was all my thoughts in one place on what this future LearnVest company, LearnVest stood for Learn, Earn, Invest.”
Von Tobel Dropped Out of Harvard Business School After 90 Days
“So I entered business school in September of 2008, and I actually took my leave of absence from business school on December 18th of 2008, so I was there about 90 days, and I'd written my business plan”
Von Tobel: New York Had Almost No Tech Startup Community in 2008
“There was not a startup community truly in New York”
Von Tobel Bootstrapped LearnVest With $75,000 Saved From Morgan Stanley Bonuses
“So I had from all of my bonuses and everything from Morgan Stanley, about 75,000 dollars.”
Top New York Software Engineers Cost $10,000 a Month in 2008
“One engineer was about 10,000 dollars a month. One really high quality engineer in New York.”
Von Tobel: Entrepreneurs Who Survive Downturns Can Thrive Anywhere
“If you can do it in this environment, you can do it anytime. Like, they were like, the entrepreneurs who survived through this, it's like a gauntlet, right? It's like, literally, it's like multiple, like, jumping through knives and hoops, and if you can get th…”
Von Tobel: Traditional Bank Branch Hours Were Irrelevant to Millennials
“Banks at the time had these stupid ads on TV that were like, we're open on Saturdays from, like, 11 to two, and you were like, what? Like, that's so irrelevant for a young person who doesn't even want to walk to a bank.”
LearnVest Reached 10,000 Sign-Ups in Its First Month
“In that first month, we had about 10,000 people who had signed up.”
LearnVest Raised Just Under $5 Million Led by Accel
“So we ended up taking, ah, just under five million dollars from Excel Venture Partners and a bunch of other really cool people and entrepreneurs threw in some money at that point.”
Von Tobel: Most Traditional Financial Plans Cost $2,000 to $5,000
“Most financial plans cost two to 5000 dollars.”
Von Tobel: Big brokerage firms ignore clients with under $250,000
“Big brokerage firms don't really want to talk to you unless you have over 250,000 dollars, which most of America doesn't.”
Von Tobel: People are either internal achievers or external competitors
“What I figured out is there's two types of people. There's competitors, and there's achievers. And achievers wake up with their own to-do list of things that they want to do by the end of the day, and kind of focus on getting those things done. And it's very m…”