Entrepreneurial Flexibility vs. Institutional Scale: Career Decision Advice
I’m weighing two exciting career opportunities and need advice.
Option 1: I’ve been running and gunning deals for an individual investor who’s looking to deploy about $5MM in equity over the next year. They’re offering me a more independent broker/acquisitions role with a salary, acquisition fees, and a promote structure. I’d have significant flexibility and autonomy, which is appealing. The market fit has been proven with them, and they’re ready to execute.
Option 2: I’m expecting an offer from a local industrial platform to step into a “VP”-type acquisitions role, leading their efforts. It’s a more structured environment, with the added benefit of working with a larger fund, giving me more “runway” and clout for deals.
Compensation for both roles is better with Option 1 (similar salary, more acq fee and 25% promote after 8.00% pref), but overall scale and runway is less than Option 2. So it comes down to career trajectory and working style. Do I lean into the entrepreneurial flexibility of the independent route or go for the stability and scale of the institutional platform?
What would you do in my shoes? Any insights are greatly appreciated!
Can you do both? How much work is actually involved in option 1? With $5mm you can buy ~$20mm worth of real estate, which is decent, but not sure if it's enough for a full-time job. What is the typical deal size? Are you purely just acquisition/sourcing deals or do you have other responsibilities like asset management? I work with similar equity/investment sizes and if my only job was focusing on acquisitions and sourcing deals, I would have A LOT of down time.
This is a great segway.. While the deal size with this investor might be smaller, the flexibility of this role opens up other doors. I understand that his sole criteria may not fit a full time job. Any time spent hunting deals that don’t fit their criteria—whether due to size, geography, asset class, or yield target—doesn’t go to waste. I can broker those deals through my existing marketplace relationships and capitalize on opportunities that would otherwise be left behind if I were tied to the constraints of Option 2.
How does the broker part work? You find a deal (off or on market) that doesn't fit your investment criteria, so then you try to find another buyer to broker a deal for that asset? Let's say the deal is on market and there is already a listing agent, you would then find a potential buyer and connect that buyer with the listing agent and then expect to make a commission? Isn't that the equivalent of me seeing a SFH on the market then telling my friend about it and if they buy it, I get a portion of the commission? That's not going work especially since you don't have an exclusivity agreement with either the seller or buyer. For off-market deals, are you proposing that after you pass on the deal yourself, you act as a broker on behalf of the seller and try to sell the asset for them? Once again, I think this is wishful thinking. It's very hard to sell real estate without exclusivity with the seller for several reasons 1.) When you go out to market this asset, you can't provide the address to the potential buyer because if it is a good deal, the buyer could undercut you and go straight to the seller. But if you don't provide the address, how can the buyer evaluate the deal? 2.) You are competing with all the other agents that the seller has reached out to. If you spent months working on marketing this property and another broker finds a buyer before you, well then you're months of marketing was for nothing 3.) Generally when sellers refuse to give exclusivity to you it means that they aren't very serious either about selling or about you. However, if you are referring to working for the individual investor and filling your downtime by being a real estate agent and getting exclusive listings to sell, then sure. But I wouldn't group the two together. You work two jobs. One as an acquisitions guy for this investor and the second as a broker. Plenty of people work a full time job and sell real estate on the side.
To answer your broader question of which option to pick, it depends. Option 2 is a standard, safe acquisitions job and climbing the corporate ladder - not much to discuss. Option 1 is more interesting but also riskier because you career and livelihood is almost completely dependent on this investor. Who is this investor? How do you know him? Do you trust him with your entire career? How long have you been running and gunning deals for him? What is his strategy and what does he primarily invest in? Do you believe in this strategy? What happens when all $5mm is invested? Is there more capital to invest or would it be time to sell some assets and redeploy? What is your plan B if shit hits the fan and his portfolio blows up or he fires you?
If you're one of those guys on this site who have the mentality of "do my own deals one day or die" then Option 1 does sound attractive because you have capital right now to back you and if you take option 2, that capital may not be there anymore. However, as with any entrepreneurial role, there is a lot of risk. The primary risk I'd be concerned with is how much do you trust this guy since your career is literally in his hands.
I faced a nearly identical crossroads 12 months ago and picked my version of ‘option 1’— option 2 will always be there in some form, but option 1 is a rarity.. bet on yourself and let it rip
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