Lessons From Working in PE, Hedge Funds, AND VC

ELI5 / TLDR

A guy named Kevin Jen worked at almost every kind of money job there is — investment banking at Goldman, buyouts at Apollo, the giant SoftBank Vision Fund, a hedge fund at Soros — and then quit it all to start his own venture capital firm. This interview is him explaining what each of those jobs actually feels like day-to-day and why they’re so different from each other. The honest headline: the hardest part of running a fund isn’t picking companies, it’s begging strangers for money. He talked to over a thousand potential investors in one year to raise his first fund.

The Full Story

The three buy-side worlds are not the same job

Most finance people aim for one of the “buy side” tracks — private equity, hedge funds, or venture capital. Kevin worked in all three, which is rare, and the interview’s real value is hearing how differently they operate.

Private equity (Apollo) was about deep number-crunching and legal grinding. You build elaborate spreadsheets, argue over fine print, and hunt for cheap, unloved companies with good cash flow that you can buy and fix.

“A lot of time was spent on financial modeling and really detailed drivers and assumptions in those models… and the second area we spent a lot of time on was negotiating legal documents.”

A hedge fund (Soros) is the opposite of patient. You can buy or sell anything every single day, which sounds freeing but is actually hard — every day you must decide buy, sell, or hold.

Venture capital — what he does now — has almost no data to model. You get a pitch deck, a basic financial model, maybe some customer numbers, and that’s it. So the game isn’t analysis, it’s access and relationships: getting into the good deals, being someone founders and other investors want to work with.

“The name of the game in venture capital… is just getting access to deals, building the relationship that you have with other VCs, founders, building a reputation for yourself.”

He also flags a culture difference. PE, hedge funds, and banking reward sharp-elbowed, cold, blunt personalities. In VC that gets you nowhere — you have to be genuinely liked, because founders pick their investors and other VCs vouch for you (or don’t).

Why he left the “safe” path

Kevin’s parents emigrated from China with a suitcase and $200. That bred the standard immigrant instinct — get a high-paying, stable job. So he started safe: banking, then PE. But once he’d bought a home, built some savings, and knew he could survive a year or two without income, the math flipped. The downside was covered; the upside of doing his own thing was huge. So he jumped.

The trigger wasn’t a dramatic epiphany. A wealthy family he’d built a relationship with verbally agreed to be his “anchor” investor — the first big commitment that makes a fund real. Opportunity knocked, and he opened the door.

He left PE partly on philosophy. Apollo’s style is value-oriented, sometimes investing in struggling businesses just to squeeze out cash before they fade. He names Chuck E. Cheese as an example — a business with every trend against it. He wanted to back companies that would still exist in twenty years, not ones quietly sunsetting.

“It just felt like the businesses we were investing in were not going to be the businesses that would be around for the next 5, 10, 20 years.”

Fundraising is the brutal, lonely part

The standout section. To raise his first fund (Fund One), Kevin spent roughly a year and talked to at least a thousand potential investors — called LPs, short for “limited partners,” the people whose money a fund invests. He traveled 40–50% of the year, doing eight back-to-back one-hour meetings a day in cafés and conference rooms, city after city.

“It’s a very uncharted and kind of lonely journey… it’s never easy asking people for money.”

The lesson he kept relearning: fundraising is mostly luck, noise, and randomness. Some investors said yes in one 30-minute call; others ghosted him for six months then suddenly wired in. His job wasn’t to convince everyone but to find the people his story naturally resonated with — which, as a first-timer, turned out to be wealthy individuals and family offices, not big institutions (many of which got burned in the COVID-era venture bust and can’t legally back a brand-new fund anyway).

He also surfaces a permanent treadmill: you are always fundraising. Even when you’re not raising, you’re building relationships for the next fund, because cold-pitching a stranger in a three-month window is far harder than calling someone who’s known you for a year.

A hedge-fund habit he smuggled into VC: take chips off the table

This is the most transferable idea in the interview. His Soros mentor drilled in a discipline: when a stock hits your target price, sell — you no longer believe it’ll go higher, so why hold? Most VCs never think about exiting at all. They just let a company sit until it dies or goes public.

Kevin applies the discipline to his startups. Every investment is underwritten to return at least 10x; the upside case might be 20x to 100x. If a company actually reaches that upside, he sells a slice — say 20% of his stake — and hands cash back to his investors.

“There’s very few LPs out there that will be disappointed or angry that you liquidated 20% of a position that’s gone up a ton.”

Yes, if that company later 1,000x’s, he gave up some of the gain. He’ll take that trade. Returning investors their original money first (“their basis”) proves he’s treating their capital like his own, and it protects against the world changing — a pandemic, a crash — while still keeping 80% of the position exposed to the upside.

Stories from inside SoftBank and the Masa napkin

Kevin joined the $100 billion Vision Fund early, and describes it as “a really well-funded startup.” No titles at first, no standardized pay — the boat was built while sailing. The upside: junior people took on partner-level responsibility, like presenting deals directly to founder Masayoshi Son (“Masa”).

The best anecdote: Masa, when he loves a founder in a meeting, writes a term sheet on the spot — sometimes on a whiteboard, sometimes literally on a napkin. The legal team would get a photo of a napkin with a few scribbled words — valuation, investment size — and be told to turn it into a binding document.

“It’s like this is a term sheet that was written on a napkin. Now, make it legal and binding.”

The point wasn’t the napkin. It was deal-making psychology: fly a founder to Tokyo, sit them in a huge boardroom with an entourage of advisors, lock down the big terms while the iron’s hot, and make them feel they’re signing the deal of their life. Strike fast, charm hard.

Hiring: trials over interviews, and the “always on” test

Kevin doesn’t trust interviews. He prefers a trial period — work together part-time for a month or two — because that’s the only real way to know someone. Most of his full-time hires started as trial hires.

When he does interview, he probes for two things. First, competitiveness: “What’s the most competitive thing you’ve done?” He figures most candidates clear the smarts bar, so the differentiator is drive. Second, responsiveness, which he calls being “always on” — and he tests it with little traps. How fast do you reply to an email? If he asks you to text after a call, do you, and how quickly? If he offers a weekend or late-night meeting slot, will you take it? He’s screening for people willing to work outside 9-to-5, because a startup fund isn’t a 9-to-5.

Key Takeaways

The three buy-side careers are structurally different: PE = financial modeling + legal grinding on cheap/distressed companies; hedge funds = daily buy/sell decisions with abundant data; VC = relationships and deal access with almost no data.
“LP” (limited partner) = the outside investor whose money a fund deploys. Raising from them is the core, hardest task of running a fund.
Raising a first-time fund took ~1 year, 1,000+ investor conversations, and 40–50% of the year traveling. The process is largely luck and noise; the skill is finding who your story resonates with, not convincing everyone.
You are always fundraising — relationships for the next fund get built years before you ask for money.
First-time funds resonate most with wealthy individuals and family offices, not big institutions (many soured on venture after COVID, and many can’t back new funds).
Hedge-fund discipline applied to VC: underwrite every deal to 10x base case; when a winner hits its upside target, sell a slice and return capital. Most VCs never plan exits at all.
Fundraising is more listening than pitching — figure out what the investor wants; if your offer doesn’t fit, no pitch will close them.
SoftBank’s Vision Fund ran like a well-funded startup early on: no titles, no standardized pay, junior staff with partner-level responsibility.
Masa’s deal tactic: lock the big terms (valuation, check size) fast — even on a napkin — using boardroom theater and urgency, then let lawyers fill in the rest.
Hiring filter: prefer paid trial periods over interviews; screen for competitiveness and “always on” responsiveness via small real-world tests.
Career framework he triangulates on: where the world is going, what you’re good at, what you enjoy. Find the overlap fast via trial and error.

Claude’s Take

This is a competent, well-conducted interview with a genuinely unusual guest — someone who actually worked all three buy-side tracks is rare, and the contrasts he draws are concrete and credible. The “take chips off the table” idea and the fundraising reality check are the two parts worth keeping. The hiring tests are clever and a little ruthless.

The reasons it lands at a 6 rather than higher: it’s an interview, so it’s loose, and a lot of runtime goes to standard founder-podcast filler — immigrant-grit origin story, introvert-vs-extrovert, “follow your passion,” advice-to-younger-self. Kevin is also a working VC actively raising his next fund, so there’s an unavoidable layer of personal branding; the “I take chips off the table, which LPs love” point is partly a sales line, even if it’s also true. Nothing here is wrong or hype-y — it’s just that the signal-to-runtime ratio is modest for a 100-minute episode. Worth a skim for the operating differences between the three jobs; skippable if you already know them.