📰 Today's topic: Want a job in VC? Watch the fund calendar

A lot of Angel Squad members hope to work in venture someday, whether that’s full time, part time, or as a second act after a long operating career.

Nicole DeTommaso, a principal at Harlem Capital, recently joined us for an Angel Squad special guest session on exactly this topic. She broke into VC from investment banking and made plenty of mistakes along the way. Her advice was so practical that we wanted to share it with everyone.

There’s more than one door into VC

Nicole’s favorite thing about venture is that you can become an investor at almost any stage of your career, full time or part time. As she put it, you can’t be a part-time investment banker.

You can angel invest, become a venture partner, join an intern program or a fellowship, take a course in VC, or advise startups in an area where you have domain expertise. Angel investing is the most common route, because it builds a track record: it shows you can source deals, pick winners, and help portfolio companies.

Timing matters more than you think

Most funds pay their team out of the management fee, usually around 2% of the fund each year. That number doesn’t grow when the portfolio does well. It only changes when the firm raises a new fund, so funds tend to hire right after a new fund launches. Nicole’s playbook:

• Know when each of your target firms launched its most recent fund.

• If a firm just launched a fund and you don’t see a new hire on LinkedIn, ask about openings. Those firms are the most likely to be adding people.

• If a firm is about three years into its current fund, it will likely raise again within a year. That gives you time to build a relationship before the budget shows up.

• If a firm just launched a fund and already made a hire, the budget may be spoken for.

Narrow your search, but not too much

Nicole started by applying to every role she could find, which mostly got her rejections. Firms differ a lot in check size, deal type, and even what a “senior associate” does. So she suggests a short list of 15 to 20 firms that fit your strengths, with outreach tailored to each one. VCs are especially good at spotting a generic pitch :)

Show value before you make an ask

Like any good VC, show that you can help before you ask for anything. A few of Nicole’s ideas:

• Learn each firm’s thesis, then send them a founder or an article that fits it, with a line on why.

• Engage thoughtfully with their social posts before sending a DM. Nicole usually replies to people who regularly comment on her content, even if she’s never met them.

• Talk to former staff and interns. They’re easier to reach, and they can tell you how the firm really works.

One hard-and-fast rule: never ask a VC to “pick their brain.” Nicole called it a red flag, especially since many VCs already post a ton of free advice online.

Keep asking

Nicole’s final piece of advice was to be persistent. When she landed her interview at Harlem Capital, she put together a 10-page presentation on why the firm needed her. She got the job the next day.

If you want to work in VC, keep going. One well-timed message can change your career path, so send the thoughtful DM, and make sure it’s useful when it lands.

– Brian from Angel Squad

📕 Startup term you should know

Ever heard of Run rate?

The predicted financial performance of a business based on currently available financial information. VCs try to understand a business’s run rate to help them make an investment decision.

My insider scoop: Know the difference between run rate (projected forward) and actual trailing revenue. Plenty of founders take their best recent month, multiply it by 12, and call that their run rate. Hustle Fund GP Eric Bahn’s example of what to watch for: a team picks up $75,000 of purchase intent in the hour after a Product Hunt launch and extrapolates it into a $50M ARR claim. He sees “a lot of those kinds of maneuvers.”

Overheard in SF…probably

“The deck says $10M ARR. The bank says please stop.”