What would it take to go from IB to a VC backed start up

Friends have been mentioning this idea to me more and more so I wanted to open it up here.

If you are in your second year IB and ready to move on, what would it take for you to venture into the start up world compared to the typical hedge fund/PE route? My boy just left DB as one of the top analysts & went the start up route for a way lower salary and a small chunk of equity. The start up is VC backed with a series A round already in and valued around 18-20M so that small chunk of equity means something.

My question here is what type of offer would it take to not go the PE or Hedge fund route? Obviously the start up space matters but I am just referring to monetary value vs risk at a start up vs sacrificed future pay.

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Personally, I don't really get why employees join VC-backed startups for a sliver of equity given the whole VC thesis doesn't work unless you make enough bets. Not only does the company need to succeed...but it needs to succeed the dilution your stake will undergo to produce anything remotely meaningful for you.

BTW if you got into IB you'll have 0 issues joining a VC-backed startup. They're routinely run by people that are luckier-than-smart.

 

Your buddy's equity stake isn't very liquid. He might be very bullish on the company's prospects and want to assign value, but m_1's point stands: most VCs investment strategy revolve around a large number of small bets with the understanding that ~90% of investments will lose money, some will do okay (1-3x MOIC) and a small percentage of homeruns will make up for the losers (plus a nice total return). The expected value of a VC fund's total investments is positive in theory, but the median investment will be a loser. 

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I did ER -> VC -> startup so I can share a relevant perspective and why the move made sense for me. For one, it CAN'T be about the money. The reason you do the move is because you want a certain kind of work experience so you can move around the industry's ecosystem. Maybe you want to become an operator and remove yourself from being siloed as the finance guy so you take the startup because the experience they're offering builds the skillsets/connections you want.

People tend to do finance for the lifestyle that comes with the income you generate. You jump into a startup because the startup work itself is the lifestyle you generate. 

For me, I fucking love cannabis and everything about it including the problems in the industry. Smoking weed is one thing, but I care even more about professionalizing the industry and working towards rectifying the damages wrought from the war on drugs. Making a lot of money in finance and investing in cannabis companies wasn't going to cut it for me; I wanted the blood more than the glory and the reason I did finance in the first place was to gain a network of trustworthy people who could point me towards the right cannabis company with the right people. I was okay with the (massive) pay cut I took because I've been expecting that since the beginning. 

Equity is sprinkles on top, nothing more. I don't expect some big exit in 3 years but I do expect to generate a network in the industry as I continue to prove my operating chops and expertise and that's what's most important for me: I want to be well-reputed in the industry by 30 and see where that takes me. 

Created a 1-step skincare solution for men. Purchase + reviews appreciated: www.w34th.com
 

Wow small world because my boy actually was thinking of joining a cannabis based start up. But I get your point. The start up lifestyle is a complete 180 from the wear and tear of banking. I personally come from an entrepreneurial and start up background so I didn't experience the banking world, but I already have seen that connections are everything in the VC and start up life. I personally think its a more fun and exciting life but I also realize I will not make the same amount of $.

I am curious though what exactly is your end goal? Are you hoping a start up hits & you exit with a couple mil in a few years or are you just in it to grow the network as large as possible then reassess from there? 

 

My end goals have changed so damn much that I consider it a loose north star orientation lol. As of right now, I'd like to eventually start my own venture or move up to a more senior role elsewhere; both require knowing the right people and being patient with it. Part of it depends on what opportunity presents itself as I continue on the journey and how my priorities change at that point. 

For now, doing well at my job, expanding the network, and staying sane during COVID are enough to focus on haha 

Created a 1-step skincare solution for men. Purchase + reviews appreciated: www.w34th.com
 

Yeah I get that. I currently am in my own venture rn too which is helping me stay sane during COVID. We are building a social stock app called Iris to try and leverage the huge influx of new retail investors. Start ups just have a sense of creativity that can't be realized in more traditional jobs. Also feel like you learn a ton more since you kind of have to be a jack of all trades to truly succeed.

 

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