How many people truly become entrepreneurial on this forum?
Is it common for people in commercial real estate to eventually be entrepreneurial, and the entrepreneurship is related to what their corporate work (am, acq, etc.)? Or do most people get stuck in the golden handcuff? What type of roles leads you to entrepreneurship faster
Few, just like in real life.
Also, remember that this site skews young. Very few older people stick around. Even if someone is going to be entrepreneurial someday, they may be nowhere close to that at 24.
Very true, I am nearing this stage now and hardly ever get on here anymore
Very few people end up going out on their own. You need experience to go out on your own and by the time you get that experience, you’re making enough at your day job to not warrant taking unnecessary risks. Making a few hundred grand a year to even seven figures and above is plenty enough for most people and that’s why you have the “golden handcuffs” situation you’re thinking about.
You also have to worry about capital raising and random operational BS. You’re better off keeping your day job and doing smart deals on the side after your grind years as an analyst or associate.
This is a really good point and one I think most people overlook. We sit here and do our job and that's all we see, but there is a massive amount of work going on in the background on the operational and logistic side. Put things like asset/property/portfolio management aside for the moment. If you want go out and start your own shop, you need accounting, you need bookkeeping, you need HR. You need to deal with insurance claims and legal issues. Want to form an LLC? Gotta go publish that (in NY, at least, maybe other states) and make sure not only have an annual meeting, but keep minutes.
There are a million and one little things that go into keeping a business running, and relatively few of them involve what your current day to day is (finding/underwriting deals, entitling land, construction management, etc). Yes, you can outsource some of these, but that gets expensive quickly. And none of it is hugely difficult, but it is really time consuming when all you want to be doing is growing your business or executing on deals.
None of this is a secret, or rocket science, but it's really easy to take most of it for granted, especially when you work in a large organization and all of it happens in the background.
Used to work for a small regional family run operation. Very boots on the ground. You can tell it was very stressful for the owners. I know one of them had high blood pressure. His son had sleep issues. People think they're chilling on yachts and playing golf. Far from it. High leverage and large time commitments result in enormous stress.
I learned everybody wants to be the boss until you become the boss. Making $250K salary and getting your evenings and weekends and not thinking about work is not as bad as it seems.
Yeah. If you're very, very good and very, very lucky, you get to live that yacht and afternoon golf lifestyle... but only after a few decades of success. The first decade you're building a business, building a pipeline, and the money only starts coming in towards the end. Then you spend another decade consolidating and expanding and hiring people to do all that work for you. Then and only then do you get to coast a bit and let other people make money for you. And even then... you gotta pay more and more to keep talent.
yeah, knew lots of guys who got burned out keeping up with the LLC formation and annual minute keeping...
Yeah I thought I had it all figured out too. Set up an S-Corp, this is easy. Then you have to do payroll. I'm paying one employee, myself, once a year, simple, right? Nope, it was a nightmare. Countless hours wasted trying to get very simple questions answered. This was pre-chatgpt so maybe things have changed. Yes it's tax-advantaged but it's also tax-complicated.
Went back to W-2 (not strictly b/c of admin stuff - but it was a factor) and have never looked back.
How much do you value being (relatively) worry-free and sleeping easy(er)? It's very real.
I assume this is sarcasm, but you are entirely missing the point. Of course it isn't a huge lift to do this stuff. But in aggregate, it is. And FWIW, the annual minute keeping is insanely important. There is basically no point to the LLC structure if you don't, because on the off chance something catastrophic happens (the entire point of an LLC to begin with) if you don't actually have those annual minutes, it means a judge might allow plaintiffs to reach through the LLC and pierce the veil and come into your pocket. You have to actually show it's a legitimate single purpose company, and that's one of the main ways you do it.
I want to see this as a WSJ cartoon
that's the filter and the moat, otherwise everyone would just do it. you gotta put up with the bullshit when you're an owner
You need a budget and plan to automate via tech or delegate all the essential non-revenue generating operational activities while you focus the revenue generating stuff. Ofc you would still need to make sure operations are efficient so profit margins are good as well.
What's your definition of entrepreneurship? Syndicating equity, raising a fund, buying personal deals on the side or something else?
Starting to stack up K-1s and minority interest stakes from my family office role but am still 95% financially dependent on the same people who pay my W-2 even if the entities, structures, and compensation package has become more complex.
Truly? 1 in 1000….
Hypothetically? Everyone will be “doing their own deals” on this forum.
I ended up forging my own path. I first discovered this site in 2016, around the same time I realized that medical school and becoming a doctor wasn’t the right fit for me. What I came to understand was that what I really was to be an entrepreneur.
I worked in development and acquisitions in a large city and left shortly before making too much money to leave.
Today, I’m a partner in a development company that has built more than 500 units, with another 350+ in the pipeline. I also buy and flip roughly a dozen single-family homes each year, while growing a construction company alongside that.
One thing many people outside of entrepreneurship often underestimate is just how expensive employees are. For most individuals, their largest recurring expense is probably their mortgage or rent, which might be maybe $2,000 to $6,000 per month. Many people might look at a $72,000 salary and think, “That’s not much.” But viewing it as a business owner is very different. That same salary means committing to pulling $1,400 to $2,800 out of the company every week or two—regardless of whether the business made a profit that pay period. And that doesn’t even account for payroll taxes, benefits, insurance, and other overhead.
It changes how you think about labor. For an entrepreneur, employees are one of the biggest financial commitments you make, and carrying that responsibility can be a hard pill to swallow.
Thanks for sharing
I admit I don’t want the hassle and stress of starting a firm. I did when I was young and hungry. Life changes and many young bros eventually realize that breaking out of the Matrix isn’t as just taking a red pill. Seeing what the owners of my previous small shop had to do in order to get started (two jobs ago) made me realize I wouldn’t want to do it.
Seems like the consensus is pretty clear very few people actually go fully entrepreneurial, and it’s not just about skill, it’s about timing, risk tolerance, and lifestyle trade-offs. By the time most people have enough experience to go out on their own, they’re already earning well and the “golden handcuffs” become real.
What stood out to me is how underestimated the operational side is. It’s easy to think entrepreneurship = deals, but in reality it’s also admin, legal, payroll, capital raising, and constant stress. That part alone probably filters out a lot of people.
The idea of doing deals on the side while keeping a stable job honestly sounds like the most practical middle ground still entrepreneurial, but without taking on full risk too early.
Reading the comments, I think there is an overestimation of how available “Golden Handcuffs” are given.
It’s probably like a Bell Curve: 20% on their way to big company success (true golden handcuffs), 60% will be the foot soldiers or bounce around (earning a living), and 20% won’t make it in the industry or are “functional deviants” (talented but don’t fit the big company culture).
Mixed in there are kids of real estate families working at big company analyst programs (about half my peers were). Those who heard the stories of how their families started their firms, and grew up not fretting the “small stuff” that W2 people (I see in the comments) see as barriers to trying entrepreneurship. That stuff is already handled by someone and they look immediately to what’s beyond.
*I recommend a Delaware LLC (forget state LLC’s that make you take meeting minutes). Foreign file.
**also there are services that help you with compliance and formation. I use Anderson Advisors, and I probably formed 30 LLCs. I use them for tax planning, structuring. $50 a month or around there.
Like many industries, but maybe more so for CRE, 1) macro downturns and 2) career progression ceiling hits at a firm. Layoffs and terminations happen.
Do you immediately look for a new job? Or do you explore entrepreneurship a bit?
Also, nobody mentioned the various degrees of entrepreneurship.
I think most first time entrepreneurs in CRE are not going solo. They partner up, and a younger partner brings something to the table (energy, big company experience, knowledge of structuring (partnership agreements, purchase and sale agreements, GMAX, etc), technical expertise such as entitlements or managing designers or contractors, a deal) and the other partner brings experience, money, and/or relationships.
There are older people out there with substantial net worth looking to start their own companies for the first time in their 40’s and 50’s, who would not be able to pull it off without a partner to help them.
Unexpected third party involvement can shake things up in ways. Entrepreneurship is not just for the young. It can be an unfulfilled desire of even the most veteran business executives.
There are so many variations too. Service companies to asset intensive companies. Advisory to investment.
So the entry point might not be full blown Captain of the ship entrepreneurship, but a junior partner/co-founder role.
Once you see under the hood, the mystique goes away. It’s really just people making things up along the way, at all ages.
This should be the top answer.
great feeback
This, plus people have a very narrow definition of what entreprenuership is. I would argue that the way brokers operate in the industry qualifies them, some disagree. In my world, if you generate your livelihood through direct output you are an entrepreneur be that at your own firm or embeded within another company.
Would be interested to hear about CRE-adjacent businesses too. Like office cleaning, parking lot maintenance, property management, etc. Seems like a pretty decent recurring revenue stream depending on how much you can scale.
Do not get into property management trying to make money, much less easy money.
My buddy got into it, but he bought an existing business. I think it was doing about $300k net and he bought the business and the real estate for $525k. It was a good deal.
Starting from scratch would be tough though.
Leaving a job making a good salary for uncertainty and no paycheck is not something that interests a lot of people
I would argue that it is actually significantly higher than most people on this website believe. Mostly because the aggregation of personality types for this website is highly skewed towards people who are very far from entrepreneurial personality types.
Let's think about this for a second, in the RE industry I would argue that the vast majority of the roles are classified as entrepreneurial roles. About 1/3rd of all people in the real estate industry are brokers. That is an order of magnitude higher than any other industry. Brokers are essentially entrepreneurs; they just have a corporate marketing framework.
Lol no they aren't. If you want to dilute the definition of "entrepreneur" to such a level, then homeless people on the streets qualify, too. Moreso, in fact, since they don't have the backing of a massive corporate machine behind them.
What a joke.
Brokers are absolutely entrepreneurs. Just becuase you don't start your own company does not mean you do not have an entrepreneurial endevaor.
All I see are excuses as to why it’s too hard. Entrepreneurship is not for everyone. Yes, it takes sacrifice and yes it’s hard work, but it’s absolutely doable. Most real estate professionals (or any professionals for that matter) don’t become entrepreneurs because they’re scared of failure and what other people might think; they’e lazy and not passionate, nor focused on the right things (focused on money rather than building a great product); they don’t want to sacrifice their lifestyle; or they waited too long in order to be perfectly prepared and got old / missed the boat.
This is all human nature and perfectly acceptable. Theres nothing wrong with a W2. But at the end of the day, there’s huge value to being your own boss in control of your schedule and in a position to make real money. You choose how you work. You can choose to be a CEO who’s immersed 24/7, or one who’s built the systems to delegate effectively, or have simply chosen to run less hard/fast so you can attend all of your kids’ sports games. There are no rules or one-way paths. It just takes passion, dedication, and a little luck. Where there’s a will there’s a way. It doesn’t need to be an absolute slog because if you love what you do, that’s called play.
I left my high paying W2 in my 30s to build my own RE business. It took tremendous sacrifice for me and my family in terms of living below our means for years to hoard cash and build a safety net to get us through the first few years of little to no income comfortably. To my surprise, all of the senior non-founders at my W2 said they wished they had tried, but didn’t for some of the reasons noted above. You have one life to live and if starting a business is a goal of yours, then don’t let excuses get in your way. If you’re comfortable chilling on your W2, then that’s cool, too, and maybe even a superior way to live life. But I’m wired differently to achieve and live outside the box.
I agree with much of what you are saying. Would you say it is easier to start a new company in RE during the middle of a boom, vs during a downturn?
I started in 2016 and benefited from price appreciation and a refinance before the pandemic hit. That was fortunate timing.
I’ve also helped or advised friends who were starting on their own post-2022 and it seems like a harder road.
What advice would you give people looking to try RE entrepreneurship in 2026?
It’s definitely easier to make it work in a booming economy, but in a booming economy everything also looks expensive. Right now it’s especially hard to raise capital, but historically the hardest times to raise capital have been the best times to invest. I think it’s impossible to time something like this. It’s always a hard time to invest and the future is never knowable, so if you want to start a business then just go start one. My one piece of advice though would be to find your edge / what you do differently or better than others. Trying to copy cat someone else’s model is doomed to fail unless you have something that truly differentiates you.
I think it is less about excuses and more about being transparent about the challenges associated with doing something on your own. I think people get a very distorted view of what is actually difficult about being an entrepreneur, or romanticize it, and that's why they fail.
I think most people on this forum will understand the economic and financial burdens and sacrifices of entrepreneurship. It's the organizational and logistical shit that might fly under the radar and sink a new enterprise, so it's worthwhile to highlight those pitfalls.
This is me right now. Working on making the jump by doing my first deal off the side of my desk. My nights are shot bc I am working on my side business and weekends I take Saturday off. Right back to work Sunday night. Figure it’ll take me 1 year or so to get a deal done in this environment. I’ve made 22 offers since end of November.
That’s wild. I did something similar, although the first deal I ever put an offer on I closed. I didn’t re-trade it either, even though I was tempted to, and I’m glad that I kept the buy clean because that seller turned out to be a goldmine relationship for me. That was in late 2021 and it’s been a home run (unlike most deals of that vintage). Definitely got lucky, but I also knew what I was looking for.
Mind sharing your buybox and market? I'm a couple steps behind you but ready to fire things up so would be nice to hear what your journey is looking like right now.
About to be a few more if I can help it.
I went the entrepreneurial route in 2022, perfect timing...haha... It was myself and another partner who is a bit older than me and had the resume / name familiarity. To other's points - this has been the worst capital raising environment in a long time.
Feel pretty fortunate and blessed. We've done just over $500M in deals since inception and worked with some household LPs and have a decent sized rolodex of groups. No sales yet but we're eying some that should be nice sized wins.
The high's are awesome but that comes with significantly more stress and worry. You're never actually "off". Getting a deal awarded is not even half the battle at this point. It's the equity. Dropping a deal, not only costs you reputationally but actual dollars that we're funding.
As a pure deal guy previously, I've learned a hell of a lot more some of which is instrumental to running a company and some is just admin work that I have to do now given we're lean. Company cash management, Co-GPs, etc.
It's definitely not for the feint of heart. Try to remain grounded and appreciative of the wins as we get them. Have thought about posting more when there is eventually more time.
Very few, but you see more entrepreneurship in RE than you do in fields like IB.
Yes. Slightly off topic, I opened a restaurant because I felt the Indian food scene in my city was mid. My most directly applicable experience going in was knowing how to negotiate a lease and build out a space. It's been going well so far.
I'm also considering moving into asset management, but I'm still working through how to properly structure the company legally. The runway for clients is already there though. Honestly the real issue is just putting in the time and energy to build it.
I always heard restaurants were a shit business… low margin, highly competitive, etc., although the Greeks and many others have figured them out… I hear liquor and breakfast are where it’s at. If you can build a successful franchise, that’s probably pretty attractive. I will never dabble there though (other than some ancillary component of a hotel or the like).
It’s brutal. Low margin and cant sell em for much of anything (in terms of multiple) but from my understanding a successful one = serious cash flow coming on relatively little principal investment. Like 1 year or less payback if you can really boom.
How many get there? 1 out of 50? How many of that 1 out of 50 are paying themselves a decent chunk and not investors?
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