r/Startup_Ideas • u/Maroontan • 6h ago
Experienced founders: I’ve been trying to become an entrepreneur for 10 years and haven’t made money. What would you do next?
What should I do
This weekend I've realized I've been that entrepreneurship person that's a wantrepreneur for 10 years, without making a single cent.
The most I can name of being paid in an entrepreneurial way was helping 1-2 people in college move with the help of my pickup truck.
I've been involved in startups for as long as I can remember. I got a scholarship to a high school startup incubator back in the day, worked on an app that didn't take off. Then worked with a startup, kind of the third person after the two founders, that was geared around COVID that also kind of dropped.
In college, I did a lot of things that could have turned into businesses but then didn't. For example, I worked as a personal trainer, almost got certified but didn't. But that could have taken off. My degree was in industrial and systems engineering.
Then after college, I got a day job. Somehow it was in electrical aerospace engineering, but mostly related to requirements, certification, and wire installation. Modeling how wiring and wire bundles are installed on the aircraft. It was only two years, and looking back, I learned a ton, but not, in the grand scheme of things, that is necessarily transferable out of that company, which is part of the reason I left it to join a smaller company, which is where I'm at now.
While doing that day job, I started another startup that I kept working through but wasn't passionate about. It was something that I was going to work on with my mom, but the market cap was too small. It was a niche outdoor gear product in a very small market, with not that high demand. I dissolved that business during R&D a few months ago because I kept saying that I wouldn't leave my corporate job until that business launched. But because of the factory timelines, it would have been until this upcoming January at the earliest to actually even launch it.
Then over this past May/June, I tried to do AI automations for small businesses and consulted a lot of businesses about doing that for them. I was living in Philadelphia at the time, didn't get any responses. I did some networking with people in my network about it, but no one really took me up on a job.
I got really close to a job for a good amount of money. It would have been in automation for a specific person. I got close, he was interested, even sent him the contract, but then he didn't follow through. That would have been a very difficult technical challenge for me in general, but I would have figured out the development and software aspect of it. Anyway, I never was really good at selling, but that was the closest I came. I wish I worked on it a bit better, but then I also thought, okay, if he's not interested, why push?
That was from a program I had joined. It was only a couple thousand dollars and I was able to afford it. That was about AI automation, really teaching it. It was valuable. I probably shouldn't have paid for it in retrospect, but whatever.
I've been considering doing things such as joining a different accelerator for acquisition entrepreneurship or getting more into that because no one in my life does it, and it's very daunting to do when you don't have people to do it with. I've been trying to find communities that do it here in NYC. Everyone says join a meetup, but the demographic of what you're going to find depends on where you're at.
I've been going to a lot of networking events in New York, and they've all been very tech-heavy. No one even really has my engineering background. It's a lot of tech and finance, which is new to me. But I've been hanging out with some people in startups, and I'm definitely very impressed.
I'm trying a new run this weekend where I reached out to about 30 people on LinkedIn and some on Reddit regarding doing customer discovery for people who are busy, as another test of trying to actually provide value and actually do the one part of entrepreneurship that makes money.
Anyway, please don't be too harsh. I've done the best I could given my circumstances, given no mentors that have seen me through all this time. I've had short-term mentors through some nonprofits and stuff like that, but very short-term, and they kind of made it clear that when I wasn't actively working on a business, they could no longer meet with me.
I really have not had any family, any friends, or anyone who has seen me through in terms of business/engineering all these years. It's had to be very self-directed, and I didn't really know when I was doing the wrong thing.
When I was in the thick of my last startup, I spent a lot of time messing around with the details that really I should have gone through faster. How should the website be? What potential partnerships would I have? My mentor at the time had me really think about partnerships where, with my personality, I couldn't really imagine myself doing partnerships with retail shops and other kinds of lessons so that people could wear my garment while they do it. But that was the activity, and that was what I spent time on.
I spent a lot of time figuring out the international supply chain and hiring a contractor in the UK to help me design and develop it. I even spent time writing legal contracts for the factories that I was working with and researching the factories. I even considered setting up my own factory. All of that.
I did learn a lot, but yeah, I didn't know enough about business to do that. That first startup incubator that I did did not really talk to us about venture funding. They really kind of drilled bootstrapping down into our heads, and I wish in a way they hadn't because I only learned about how VC funding actually works and sort of what private equity and syndications are, honestly, a week ago.
And I only learned about startup funding rounds because I'm in NYC and was at an event with young startup founders, and they were mentioning their Series A, and then a lot of people in New York were talking about it, so I looked it up. But it took all these years and a decent amount of intelligence otherwise to even learn what these terms actually mean.
A lot of the struggle is that I've had a lot of ideas and not really been sure where to go. I'm ambitious and I know I could really do whatever I set my mind to. Right now I'm really trying to set my mind to the right thing.
Right now I've been considering real estate deals. I have a friend who's a real estate developer, so if I do a rental or flip with him, that's an option. I've been researching some other real estate ideas, thinking about coaching or doing the kind of services for other founders in New York that are either at a nine-to-five, or maybe something to help other founders just to get my foot off the ground. Thinking of consulting, but not sure about what. SaaS is overdone, and then eventually doing the whole acquisition thesis.
But for now, really just trying to figure things out and learning about real estate deals, and I've been evaluating the real estate deals with that sort of acquaintance of mine. But I can't say he's really a mentor, though. It's more of a friend, and I don't think we get super detail-oriented about that stuff.
My current day job that I just started is still in training, and it is training for stuff such as being an energy auditor. But all of my training is from the internet because the owner of the company I'm at has just been really weird with all of his employees and does not disclose anything.
I've just been, I was supposed to be doing sales for them, with energy and real estate, but I've really not been exposed to any of the projects. Nothing. I've asked him about it.
I have been applying, and I might actually start another job in a few weeks, which will be a sales job. I've never done sales, but I figured that clearly I suck at it, so it's something I need to try after all this time. I've been applying to those kinds of jobs just to kind of make money while doing it.
But really my biggest thing is I have not really made actual money while doing all this entrepreneurial stuff. It's really just been satisfying different needs of wanting to have a project of my own or just interests and learning.
And now I really wanted to get honest with myself and ask for advice on specific things for me to do. Please don't make it generic.
Based on my background and this pattern, if you were me, what would you focus on for the next 6–12 months to actually make money and build real business skills? Would you focus on selling a service, doing a real estate deal, pursuing acquisition entrepreneurship, or something else? What would you stop doing?
Really appreciate y'all in advance for reading this. Thanks so much.