I've had more luck with entrepreneurship than with career: advice desperately needed

I hit month 9 and I have yet to make any money from my actual day job (Commercial Real Estate Sales). I graduated in '17 and I am just putting in my time to build my resume so I can find something decent (I graduated with a shitty 2.8 GPA at non-target). I spend about a 2 hour round trip commute to work, 4-5 days a week. I also have racked up $500 Errors and Omissions insurance bill. So all-in-all I have lost money after working for 9 fucking months. I work for a bottom bottom tier shop.

My plan is to get into grad school (MSRE) and get more work experience through internships (hopefully this happens by summer). Unfortunately, this will further increase my debt burden. I am just trying to land an analyst gig someday and move up the ranks. Although recently I have asked myself for what? So I can spend 12 hours a day looking at a computer screen and building excel models? I mean, I want to develop my own buildings eventually but is this plan actually beneficial in the long term?

This all got me thinking about how I have literally had more luck will my LLC side hustles. Then I started thinking about quitting all this networking (for a job), cold-calling, being ignored, and endless job applications completely, What if I just made a living starting and stabilizing small businesses (the unsexy kind.) Do you know anyone that does this? I have always been extremely passionate about business and I was the kid running lemonade stands at 5 years old. I always sucked at school but almost always found ways to cash-in. To get to the point where I can do my own projects, I am not sure if being an employee will ever give me the capital to be a real player.

I think I have been more unlucky career-wise than most. I am certain at this point I must be at the very bottom amongst most of the people I graduated business school with. I am in the DC market and I know it is competitive but I am I crazy? I know this is extreme but after sending a contact 12 follow-up emails to follow through with a promised introduction (with no response), I have about had it. The hours spent drafting emails that will later get ignored could be better allocated building quality businesses. I am already eying a third business I want to start.

Thoughts?

 
Most Helpful

You’re too early in the process to say that you have failed. If you’re truly focusing and executing on income producing activities (making calls, getting meetings, pitching, etc.) you’re going to make money. The only people I knew in brokerage who “failed” were simply just not doing that. It’s simple but very hard to execute. It’s a long term game...think in years not months in brokerage.

But yes, an opportunity to reposition small businesses exists. Many of these assets are well positioned for consolidation as we enter into the midst of a very large scale generational transfer of wealth.

Pick something and stick to it - you’re all over the place. Which tells me you’re unsure which is okay because you’re young but don’t give up too early on whatever you choose.

I had a flair for languages. But I soon discovered that what talks best is dollars, dinars, drachmas, rubles, rupees and pounds fucking sterling.
 

PS - If you're in private client brokerage you can come across a ton of opportunities to buy (as a principal) or advise on selling businesses as there are a lot of owner-users particularly in the small balance retail property space ($1MM-$5MM) - think bars, restaurants, gas stations, pool halls, liquor stores, etc.

I know a guy who dabbles in this... killer IS broker and has rolled into a lot of deals. The canvas is yours to paint there really is no blueprint. Good luck!

I had a flair for languages. But I soon discovered that what talks best is dollars, dinars, drachmas, rubles, rupees and pounds fucking sterling.
 

20's is for learning 30's is for earning

Don't sweat. We are all trying to figure our shit out (hence we are all on WSO). As Merchant_of_Debt said, you are too young to have failed. If you give up, that is failure. If you get back up and fuck up again, that is learning.

My question is, could you do both? Generally speaking, brokerages have flexible schedules. Albeit, less sure about young brokers. Also, utilize any and all connections, even if they are "peripheral" (i.e. my dad's brother's friend is looking for space)

If you need to re position, that's great. But don't give up.

 

Just keep in mind if you want to start a business you need it to hit scale pretty fast to make real money. Even moving $1M - $2M in revenue a year on a product with ~50% COGS and you're still not really doing great.

Don't fall into the small business owner mindset/trap whatever you do. IMO being a small business owner doesn't really make sense once you work out the risk/reward math in most cases. Treat anything you pursue like an enterprise and you'll do much better.

 

That sucks bro makes me feel lucky to be in my position. I can say if you're passionate about entrepreneurship go for it man. Taco truck, vegan protein, whatever it is go for it. I declined my return offer to work at a BB, to start my own business after i graduated and stopped b/c i thought it was too much work. I ended up joining another investment bank and honestly i work 24/7 -- like a fireman who is always on call. Running my own business was at least working for myself, i didn't have a boss, and I wasn't stressed about fucking up pointless shit all the time.

I disagree with small business trap (if anything there is a corporate ladder trap). I'd say a large majority of businesses start small.... if you're passionate about what you do, then you don't have to work a day in your life. And with a 2.8 GPA you're obviously much less competitive than the other pool of candidates.

Don't want to make any decisions for you, just my .02

What concert costs 45 cents? 50 Cent feat. Nickelback.
 

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