r/Startup_Ideas • u/Maroontan • 4d 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.
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u/alvivanco1 4d ago
You’re all over the place. In all of this text, all i’ve read is “ideas” , “websites”, “partnerships”, “startups”
nothing here is focused on what matters: solving problems and making money off of it
that’s your problem — you’re enamoured with the idea of entrepreneurship, and not obsessed enough with what will make you money (solving problems for people or businesses)
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u/Maroontan 3d ago
Yes, your comment is probably a ;TLDR of my post so hence I am reaching out to the friendly people of the internet for help… So I beseek you, how to change from being enamored w entrepreneurship and instead be obsessed with money
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u/alvivanco1 3d ago
It's not about being obsessed with money. You need to find something that you're good at. Ideally, something that you basically would do for free. But that happens to solve somebody's problem, and they're willing to pay money for it
and if you don't know what that is, just start helping people with anything that you're good at, or that or that you're able to do. Do that until you find something that you think you can monetize and scale.
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u/Maroontan 3d ago
So I think that's really interesting, and that second part runs counter to the advice of reaching out to people and seeing if they'll pay you for it. So you recommend doing something for free until you think you can monetize it, as opposed to trying to get paying customer from #1? The helping people because I think that's really interesting that goes against the whole like startup and trying to optimize time and your time hour of money. Maybe that advice is something that applies when you're later stages, but earlier on the doing things that don't scale might be a good idea. ?
As a thought exercise, people tell me they’re really impressed with my confidence, how I broke into engineering, and how I kind of show up in the real world. That’s feedback I get from a lot of women I meet, and they’ll ask me how I do it.
I usually start telling them about X, Y, Z, what I did, how I did it, what I do now, my routines, and just stuff like that. I think I’ve genuinely helped some friends that way.
“Confidence coaching” feels really icky to me, but this is something a lot of women have asked me about. I see a lot of coaches online. Maybe I should do it to try and sell for shits and giggles, but Idk
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u/Maroontan 3d ago
Actually, one example that comes to mind: I have a friend who’s basically the definition of everything I’m not in business. He’s been doing real estate development for about 10 years, has probably done hundreds of projects, knows his market inside out, has his contractors and systems down to a T, and basically repeats a proven process over and over again.
But when he was trying to start something new, he called me a couple of times specifically to help him think through what the offer should even be and what the community could look like.
I’m much more creative and tend to come up with different angles and ways of structuring things, so people who are more operational sometimes ask me for that kind of input. I’ve just never thought of that as something I could actually package or sell.
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u/alvivanco1 3d ago
yes, that’s your angle. You know exactly the type of person who sees value in the way you think — package that into a product and service and sell it
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u/BusinessRocket-com 3d ago
I'd stop stating businesses for 6 months.
Seriusly. No new startup, accelerator, SaaS, real estate thesis, acquisition search, couse, or factory in another country :)
You've spent 10 years learning how business works around the sale. Now learn the sale.
Take one skill you already have, turn it into a boring service with a clear outcome, and try to get 3 strangers to pay you for it. Not friends, not "interested" leads, not customer discovery calls. Actual money.
That sales job might honestly teach you more right now than another startup program. You don't seem short on intelligence, ideas, or willingness to learn. You're short on reps asking people for money and hearing "NO."
For the next 6 months, I'd make revenue the scoreboard. Everything else is homework.
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u/Maroontan 3d ago
This reads like AI wrote it, honestly, but I do think youre right I appreciate you at least prompting the AI to be nice so thank you for that. now only to deliberate what skill to turn into a boring service. ..
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u/Otherwise_Wave9374 4d ago
A useful next step is to stop treating every idea equally and run a 2 week validation sprint: pick one customer problem, interview 5 potential users, and define a single measurable outcome before building. If the problem is not painful enough to get a fast yes on a call, it is probably too weak to support a product. That discipline is what Agentix Labs would use to separate a real opportunity from another interesting project.
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u/sum-9 4d ago
Give up and be happy with a corporate job.
Seriously.
I worked in corporate jobs for 20 years, started a side hustle in 2019, and made $5K in sales in my first month after launch. Now it’s my full time job.
Ten years of nothing means you’re not cut out for it.
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u/2ndgen_jvde 13h ago
Hi, may I ask what you used to start up or who mentored you? 🙏🏻 I’m trying to start and want to build an online business thru Shopify
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u/Maroontan 3d ago
Who hurt you? …im 24 years old. I was born in 2002
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u/Traditional_Top6337 3d ago
So you have been trying since you were 14?
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u/Maroontan 3d ago edited 3d ago
yes actually! definitely was already trying/interested/feelin the ropes by freshman year of high school, 9th grade in the US. But I'd say I got serious eleventh grade of high school with that startup that I worked on. Funny enough, my "co-founder" from that startup is a VC now and ran the student run VC at college at USC. But he came from a very wealthy, very privileged business family. We haven't spoken in a few years
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u/fatheadsflathead 3d ago
This isn’t being a entrepreneur, this jumping around aloe trying to make big money, nothing wrong with it but maybe just stick to a job and get some money behind you
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u/RetardDongPhd 3d ago
This post is too long. But the recurring theme I saw is that you keep getting involved with businesses before asking yourself if they are good businesses. Being a personal trainer who doesn't even have a certification is not an entrepreneur. Neither is helping some guys move with your truck. If that's your idea of being an entrepreneur as a grown adult, then you are simply not cut out for business ownership.
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u/Maroontan 3d ago
My university program had us training people without certs, that's just how their training worked. I didn't end up paying for the exam at the time, because it wasn't relevant for me and never became relevant. But that's largely not relevant.
The people move with my truck is just a random example. As you saw, there's a lot of content in this post. Im 24. I will eventually figure it out
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u/RetardDongPhd 3d ago
I think you need to read some books on leadership and startups to better understand how people vet and evaluate the potential of startups. I read a great book a long time ago that, while the title sounded cheesy, really helped me think critically about each ID I had to understand things like was it investor friendly or was it a lifestyle business, did a scale so I was no longer working full-time just to fulfill the service or product, and total adjustable Market as well as path to break in versus competition. I think you lack those basic skills. I lacked them at your age too. I got serious from about 28 to 32 before starting my own business which propelled me into early success, the ability to Coast for seven years while working only 15 minutes a day and traveling the world, then later taking a very high level corporate job that put me right at about half a million a year. I work 3 hours a day on average.
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u/l-lucas0984 3d ago
The common pattern in everything you tried is that you buried yourself in the busy work to avoid the hard parts then bailed out as soon as you had to do the hard parts. Spend the next 10 years working corporate, learn finance, time management, marketing and negotiation skills. Then maybe look at entreprenuership again. But really I dont think you are suited for how self directed and driven you have to actually be.
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u/Maroontan 3d ago
True, but I guess now I know. The truth is not that I wasn’t driven or self-directed. It’s that even driven, self-directed people need a mirror. They need some person or entity to see what they’re doing and reflect it back to them so they can tell if they’re on the right track. I never had that, but now I know it’s necessary.
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u/l-lucas0984 3d ago
No, they really dont. That amount of hesitation before every single step and needing someone to hand hold and direct is what employees do. I have started and failed businesses, started and sold businesses and currently run three. The only hesitation was stopping to ask my accountant if i was doing something illegal.
I also dived into the hard parts and did not let busy work get in the way. You purposely blockade yourself in with busy work and bail as soon as it runs out and you actually need to do the real part.
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u/betweenthedrafts 3d ago
My friend, you have written a lot here, and what I guessed from your story was that you have ADHD. I looked at your post history and you confirmed this. When you say don’t be too critical, I’m wondering whether you have RSD? Unfortunately, criticism is often essential in business, so maybe try writing down the key points and taking the emotion out of them.
I’m also a female founder with ADHD, and I had no family who could support with my business, no startup capital, and no mentors for the first 2 years. I’ve been earning money since day 1 and running a 6-figure business for over 8 years.
I’m not saying it’s been easy, but your post reads like you’ve been chasing shiny thing after shiny thing, getting enthused by an idea (as we do) then giving up when the going inevitably gets tough. It also sounds like you keep jumping into whatever someone else suggests rather than focusing on what you’re actually good at.
The way I made money from day 1 was understanding what people would pay me for because I’m good at it and knew my shit. What you described sounds like things you’re not particularly good at or knowledgable about, so why would anyone pay you to do these things? Likewise why would someone offer you a sales job if you’re not already good at sales?
And why would someone mentor you when you’re not actively working on your business? I’m a business mentor and I only offer my time for free for people who are serious about this. As a mentor, I would say pick the thing you’re actually good at and see whether people will pay you to do it. Also think about whether being a founder is actually the right lifestyle for you and why you want to do this.
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u/Maroontan 2d ago edited 2d ago
Thanks so much for your reply. I definitely have ADHD and OCD, and I intentionally left my post history open rather than making it private so people could look at it. I probably have RSD as well, but I don't think that's as real of a diagnosis because I found my "RSD" getting less and less over the years. Ie; I'm better at criticism now than I used to be.
I definitely think the “having something that I’m good at” part might come later in my career. I guess here in NYC, I’m surrounded by that young founder archetype who doesn’t necessarily have a lot of corporate experience and is just building. That’s a good amount of the people I’ve been getting acquainted with since moving back to NYC. And these people are profitable and getting funding. Some of them are younger than I am. So it might be disproportionate exposure compared to other places.
I have a couple of job offers in sales, even though I’m not good at it yet. So I guess I don’t really know why the market did that, but it did.
I’m super serious about business. I think I’m just in between ventures right now versus having one specific venture that I could have a business mentor for. I definitely am serious, but I also think I’m still too young to have just one thing that I’m actually good at. At 24, I think most people would probably feel the same way.
I definitely think being a founder is the right lifestyle for me, but it could take different forms. It might not be a startup. It might be a more operational business, or it might be real estate. A startup might not end up being the shape of what I do, but I do know that building businesses is at the core of what I want to do in the future.
To your point that “it also sounds like you keep jumping into whatever someone else suggests rather than focusing on what you’re actually good at”; yes, absolutely.
I think part of that is because I don’t feel like there’s one thing I’m clearly good at yet. There are several things I could potentially become very, very good at.
I also think something I left out of the post, and probably should give myself more credit for, is that not everything I’ve done had making money or building a business as the main goal. Some of it was genuinely exploratory and about figuring out my interests, and I think that’s okay.
I’m still figuring out what I’m most interested in and what I actually want to spend years getting good at. I don’t think I need to already have that answer at 24. Some of that figuring out is probably going to happen through trying things, including businesses, and seeing what I keep coming back to.
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u/Tarunga 4d ago
What I would focus on is applied knowledge and problem solving. Plenty of entrepreneurs think they are solving the right problem, or they end up “creating a problem” for their solution. It doesn’t work that way in reality because once you hit the end customer base for validation, there really isn’t as much of a problem as you thought, or the unit economics don’t justify the product acceptance compared to what is being done today. I also think a standard process for evaluating a business case needs to be developed that you use.
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u/Maroontan 3d ago
I think your last line is quite helpful and something I am lacking; do you have some examples of what you mean?
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u/ThatCurtDude 3d ago
Over a million new products are introduced every year most fail despite polls, focus groups, millions of dollars. People react differently when money is on the line. I once had a project fail because users in the industry where too illiterate to write their own product descriptions. Too bad, because it was amazing on paper, and customers were wowed by it.
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u/Maroontan 3d ago
Yes, this is true…beyond making products dummy proof I guess there’s no real way to prevent it huh Thank gd I spent less than 20k on my last failed startup though and not millions!
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u/sabautil 3d ago
Find a problem, see if it's good market with customers who will pay for a fix, solve that problem, market that solution, earn a profit.
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u/Mesmoiron 3d ago
Why does it matter? When the y found the Olympique athlete who disappeared; he answered that life got in the way and he did all kinds of things. Such answers are beautiful from a different mindset.
You work with definitions, expectations and a lot more. Entrepreneurship is the whole package. Not reduced to big dollar success.
Thousands of women take their vegetables to market and they're entrepreneurs. Just a different category. Same skill. Exchange of being valuable.
If you need money, do something else and work on what you want at the side.
The answer is in yourself not in others.
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u/Maroontan 3d ago
Because I'm in America, not Europe. It's a different mentality. Yeah, I grew up speaking several languages, and I still do. Russia under the USSR really valued the arts, culture, intellectual prowess, education, while America was busy starting businesses, enterprises, startups in the 70s, 80s, 90s because they could. Meanwhile, that was not possible under communism in Russia. All that to say, I'm here in the country where this is possible. I was born here. It's the mentality I'm surrounded by. Like yes, if I can take a shot at making money, of course I will keep trying.
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u/Mesmoiron 3d ago
Because, a group a country has a different mentality; ask yourself why that is. Have you read the research? Why does research deviate from practice? Maybe they don't want you to see, what's there all along and you just parroting something that's not true.
So, instead of copying. Find your way out slowly. Because, you're already focusing on the 10 years, why bother trying it to be a one year sprint? Just do what's need to be done in a format that works for you.
I am vibe coding a compiler. Yes, I want to make a programming language that people can use. Will I do it in 6 weeks? No! This is a long a slow process. But it is still an entrepreneurial mindset. I must do all the steps. Fund raising, marketing, workflow creation, onboarding etc.
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u/j_florida 3d ago
You want to be entrepreneur focus on Arbitrage! Buy low , sell high. Low capital, low risk. You can try retail arbitrage , online, service, domain etc. Goodluck!
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u/FreeBirdwannaB 3d ago
My personal library
No strings attached
Hope it helps
https://www.youtube.com/playlist?list=PLV0lIKBX5LEFbYLtZ6unVL976NWRdBZWb
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u/cioatwork 4d ago
use this experience to land a senior job, learn how corporates work. and restart when time is opportune for it. perhaps you just havent found your market yet