Deferring IB to be CEO of VC Portco? Plz help

Currently a second-year MBA at a target school signed to a pretty competitive product group at a NY MM. Really enjoyed my summer internship and signed on immediately after receiving the FT IB Associate offer in August. Been a bit bored but hunky dory ever since. 

Fast forward to last week when a GP (and former professor) for my school's in-house startup accelerator/VC firm reached out asking me to be CEO of one of their portcos (5-10 employees, faculty/alumni advisors, six figure seed capital, etc) and guide them through funding rounds and growth. I think its a great opportunity skills/networking wise but obviously cant do both once I hit the desk Aug/Sep '24. GP/Founders want me to drop IB offer to be long-term CEO but ideally I'd defer my start date to next years onboarding cycle (Aug/Sep '25) and run the portco through funding rounds and help find a more long-term CEO. I'd be able to draw a salary but obvi nothing close to street pay

Curious if anyone has heard of people in similar spots/how it has gone. Would the bank see the value in gaining those skills and let me hit the desk next cycle or would they just tell me to go fuck myself and start whenever they say cuz my group needs bodies. If I do delay and start in '25 would the team see that as bad teammate and stunt my career? Should I just renege on the IB offer entirely? Pre-MBA was not IB and my UG was semi-target so thinking this is my last clear chance to break into the industry. Ik im in a solid spot having this dilemma (especially given the market) and im incredibly grateful for it but I want to do it right so plz help :-( 


Background: No wife, no kids, mid20s, Pre-MBA was military and PWM at a "BB", long-term goal would be to transition to PE in <10 years. 

 

Well, you've got quite the conundrum on your hands, haven't you? It's not every day that you get an offer to be a CEO right out of the gate. But let's break this down a bit.

Firstly, it's important to consider what you really want in the long run. You mentioned a goal to transition to PE in less than 10 years. Now, both paths could potentially lead you there. The IB route is more traditional and might provide a more structured path to PE. On the other hand, being a CEO of a startup could give you invaluable operational experience, which could be a unique selling point when you're looking to transition to PE.

As for deferring your IB start date, it's a bit of a gamble. Some banks might be open to it, especially if they see the value in the skills and experience you'd gain as a CEO. However, others might not be as flexible. It's hard to predict how your team would react, but it's possible that they might see it as a lack of commitment on your part.

If you decide to go the CEO route, it's important to consider the risks. Startups are inherently risky and there's a chance that things might not work out. However, if you're successful, it could be a huge boost to your career.

Ultimately, the decision comes down to what you value more and where you see yourself in the future. It's a tough call, but I'm sure you'll make the right choice. Good luck!

Sources: Q&A: Principal at Early-Stage VC Fund, What Harvard Business School is Teaching This Tech Entrepreneur, Q&A: Leap from S&T Associate to Startup Founder, Should I delay graduation by a semester for a summer internship at a large bank?

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In many ways this is a personal decision, so take comments with a grain of salt. I have a couple years of venture + growth equity experience at places that folks here would most likely recognize.

My bias here is that startups are dime-a-dozen, particularly at the pre/seed, and those almost always are founder-led by folks who know a problem / end-market exceedingly well or are technical masterminds pushing the boundary from that perspective. It's typically whenever you have true product-market fit, significant revenue scale, a ~50+ FTE org (often Series B+) when you need a professional CEO and there are not many folks who have the skillset to scale a software company from, say $5m to $50m in ARR.

So the framework here is that if this is a company you founded, have built a small team around, raised money, etc. and in an end-market you're passionate about... go for it and don't look back. You'll probably regret it otherwise (even if the outcomes aren't ideal). But what stood out to me was your desire to end up in PE in the long run... which to me means your priority is ultimately a stable, high-paying, transaction-oriented job in which you are an investor or at least think like one. Obviously a bunch of posts here about the challenges (or lack thereof) transitioning to PE as an IB Associate, but I reckon most folks who think they'd enjoy PE wouldn't ultimately hate some variation of their career as a senior banker or corp dev guy.

 

easiest no ever.

absolutely do not take the CEO role lol

being a CEO of a startup portco isn't prestigious at all 

startup accelerators/VC firms that aren't like Sequoia are kind of ???

you mention networking but what do you actually want here?

like assume you do take the CEO role and meet some cool people. Does that actually progress your career or get you to where you want to be?

 

While the CEO title may feel impressive- sounds like it’s not to me (small team, pre-seed, small amount of funding). Its like going to work for Uncle Joe’s company. Would be a hard no for me. Ask to be on the board of this company, not CEO so you can get the best of both worlds and not get sucked into CEO title for a non-CEO job.

Like the unadjusted- only with a little bit extra.
 

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