I have enough personal runway to realistically make 0 dollars for the next 3 years.
I got to the super day for 2 mega funds and both said no.
Family offices are interviewing me but ive been that route and have worked with absolute maniacs.
What would you do? No kids, an iffy long term gf î dont think wants to get married etc.
Have personal connections to capital and would throw money my way given the fact I've done 2 side deals.
Raising equity for a first time developer as well as sourcing deals during the off-season, which has been the past 3 years because of capital market woes.
I may be 5 beers deep at a dive bar but god damn I am not happy.
Two words. Risk Mitigation.
What happens if you can't find a deal? What happens if your investors bail? What happens if you're halfway through a deal and markets turn? Any of these events can happen in the blink of an eye. So what should you do? Diversify your risk. Pursue all avenues. Unless you have investors who are willing to pay you a salary or an actionable deal where you can draw funds from to pay yourself, you need a stable source of income. It's very rare and ill-advised to dive head first into starting a business. Often times a business starts as a side gig and grows into a full time job and at that point, you must make a decision. But you aren't there. You don't have a deal and your investors are willing to fund a deal, not your livelihood (I assume). You can find a job and work on your own deals on the side as you've been doing until it is enough to become a full time, sustainable job. If your goal is to go off on your own anyways, then you can put in the bare minimum at your job while you pursue your side deals. If your side deal goes side ways, you still have a job, but if you put all your eggs into your side gig and it goes sideways, then you have nothing. Even if you have 3 years of run way, it's stressful to see your savings drain away indefinitely. Trust me, I know what it's like to hate your job and wake up every day hating life. But when your savings drain down to your last dollars and your deal has gone to shit. That job will feel like heaven.
Thanks for the reality check. Grass is always greener....
The grass is very green on this side and I encourage you to do your own deals. Working for yourself, is incredibly rewarding. Knowing that every dollar I make goes into my pocket and knowing that every tedious task I do has a purpose makes "work" not feel like work. I would even argue that even more rewarding than the money is the flexibility. You aren't tied to a desk everyday. If you want to take it easier today and push some things off until tomorrow or next week, you can do that and no one will berate you. The fact that you've done 2 deals on your own is evidence that your dream of running your own shop one day is very feasible. You just need to slowly work up to it, manage your risk, and hit your stride.
On a separate note, could you provide more details regarding your 2 side deals? What were they? What was the game plan? What was the outcome? What were the check sizes? Always curious to hear what other entrepreneurs are doing.
2 deals was raising the preferred equity tranche for a small time developer building his track record then helped him on the refi. Met him at a coffee shop which is the funniest part. I joined the industry to do exactly that but all my roles have been siloed and my friends that work at family offices or LPs that wear "many hats" hate it because it just means over worked and underpaid
If you're already five beers deep and contemplating life, it sounds like you're at a crossroads. Based on the most helpful WSO content, here's what you should consider before making the leap:
1. Personal Runway and Risk Tolerance
2. Connections to Capital
3. Timing and Market Conditions
4. Lifestyle and Priorities
5. Alternatives to Quitting
6. Mental Health and Happiness
Final Thoughts:
If you’re serious about starting your own thing, take the weekend to soberly map out a plan. Identify your first project, secure commitments from your capital connections, and outline a timeline. If you’re still unsure, consider consulting with a mentor or someone who’s successfully made the leap. And hey, maybe cut back on the dive bar beers—your future self will thank you.
Sources: How many of you actually plan on going independent?, How to start an International RE family office, https://www.wallstreetoasis.com/forum/real-estate/running-your-own-shop?customgpt=1, Millionaire by 30, Why Not Start Your Own Shop?
Maybe try to coast more at work and go harder on your side deals? Would make for a smooth transition if it works out and if it doesn’t you still have your job
What were the side deals you have done?
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