Can I turn my "passion" into a bootstrapped business?

I recently shut down my product business after five years of effort. I’m now turning my attention to trying to come up with my next idea, taking care not to head down a path that’s going to burn another five years fruitlessly.

When it comes to detecting a good business idea, I’m familiar with the advice to talk to people and try to find out what their problems are. Maybe this tactic really does work for people but so far just confuses the person I’m talking to and makes me feel like a weirdo.

I think part of my problem is that a software product could serve any industry at all, and so I have to just arbitrarily pick an industry out of all the industries in the world, which is hard.

So a thought occurred to me today that maybe I can use my interests as a starting point. I’m not a member of the “follow your passion” camp. (I don’t imagine patio11 was passionate about bingo cards or appointment reminders.) On the other hand, I can see some value in at least being somewhat interested in the domain in which you’re working. My last product was scheduling software for hair salons, and not only am I not interested in hair at all but the about only thing I have in common with most hairstylists is that we’re both homo sapiens.

And let me be clear: I realize that I should try to detect what people want to buy and then give them that, rather than decide what I want to build and then see who might want it. My thought here is that I can use my own interests as a launching off point in embarking on market research.

So here are some of my interests, in rough order of strength:

  • Music
  • Art
  • Skateboarding
  • Cars (especially BMW)
  • Pool
  • Legos (especially Technic)

And here are some thoughts on each:

Music: Every dumbass in the world wants to do a music startup. I probably better not waste my time with this one.

Art: Maybe? I actually don’t know much about art or the business of art, I just know that I like to draw and that art is just something I generally enjoy.

Skateboarding: I don’t know what kind of opportunities might exist in the skateboarding industry. One advantage here is that since I used to skate, I can talk intelligently with skateboarders, I’m familiar with prominent skate companies and pro skaters, etc. This is in contrast to the beauty industry where I knew nothing and didn’t particularly care to learn.

Cars: This is obviously a huge industry with fucktons of money flowing through it. I also don’t know a whole ton about cars beyond the fact that I like Top Gear and I subscribe to Car & Driver and one time I drove a Ferrari and it was awesome. My favorite kind of car is BMW. I don’t know if that helps me get pointed in a direction at all or not.

Pool: Pool has become a hobby for me lately. I know nothing about the pool industry but I find pool to be interesting.

Legos: I could play Legos all day every day for the rest of my life. I know it can be dangerous to base a whole business on the back of some other single business. You don’t want to be dependent on someone else’s whims. But I also imagine it could be done in a safe way, like if a person were to write a book about Legos. I’m not going to write a book about Legos, though. I would want to use my existing skills.

I think that’s about as far as I can get myself with this idea, at least for right now. What I think I’m missing is the next step. If I were to choose to pursue something in the auto industry, I guess I would go ask people in the auto industry what problems they have or something, but how? Go to a dealership? The guys there who are available to talk are probably too low on the totem pole to answer me in a meaningful way or even understand where I’m coming from.

I’m totally lost and could use some help. I’ve been trying to come up with a product business idea for eight years. I’ve made six attempts at a product business in those eight years, all failures. Something is clearly wrong with my approach but I can’t figure out what.


My own approach has been:

-Find a pain point in my own life that can be solved with software and that I think would be interesting to work on.
-Talk to a few people and look at the competition.
-Launch a very rough v1.0 ASAP and see if anyone is interested.

In the last 11 years I have launched 3 software products. One has done very well (PerfectTablePlan), one flopped completely (Keyword Funnel) and the third was one is showing promise (Hyper Plan). When I launched each one I had no idea whether it would be successful or not. I wish I had launched the failed product a lot earlier.


My issue with “passion businesses” is if it ends up being a B2C play which I think is v hard to do successfully as a bootstrapper (read, requires a BIG dose of luck). If you can go and talk to people operating money making businesses in any of those verticals, hopefully people you already know due to your interest or people you can at least go and meet somewhere without it seeming totally weird maybe try your conversations with them.

Maybe instead of trying to ask them about their problems, ask them if there is something you could build for them if you gave them a week of your time for free? That could be a jumping off point for a discussion about what problems they think they have which could be solved with software. Obviously, be clear about your intentions and be sure to clarify that if you built it (and it solved their problem) that you’d expect them to pay something for it. But, what would that price be do they think? Also, remember to ask if they know anyone else who might be interested in having the same problem fixed.

Good luck!

1 Like

+100 for this. All of those things on your list are primarily hobbies so B2C.

Even the car as you’re only seeing it from the hobby site, you don’t have an interest in, e.g., software to help with the logistics of dealers demonstration cars.

Guess your aware of Amy Hay, UnicornFree, 30x500 etc which seem to be one of the goto resources for ‘figuring out your niche’?

Music: Every dumbass in the world wants to do a music startup. I probably better not waste my time with this one.

You can’t seriously think it’s Spotify or bust? Music is an enormous market, there are multitudes of niches to be explored.

The areas you outlined are too broad. Look for sub markets within those areas. The snow-plough market. The adult Lego technics market.

As an aside…

I get the feeling from your closing-down-of-Snip post and this thread that you quite easily find problems and reasons things may fail. That’s ok, any smart person does that. But it gets poisonous if you allow these thoughts to take hold.

I’m not saying you should plough on regardless of your analysis. But you should also be aware that sometimes your analysis only goes so far and you need to broaden your thinking a bit because otherwise you might be missing something.

I think, specifically, you should hone in on some much finer niches, work out what you like about music, cars, pool etc and work out what you could do there.


Thanks for the responses. I want to clarify: I don’t mean that I think I should go after a B2C market. I just mean that I imagine it’s probably better to go after a B2B market that’s at least tangentially related to my interests (e.g. software for car dealerships) than something like the beauty industry where I have no interest at all.

@Rhino Yes, I’m aware of 30x500 and planning to join when I can. I believe it has only opened up once since I killed Snip, which was a couple weeks ago, and I just didn’t enough money.

I’m in a similar position - I’m currently shutting down a bunch of old software product that make enough for a cup of coffee every month. In general I have not been successful at business. Either running a consultancy, or products (the pay off has been an accelerated path to ‘proper’ job).

Once everything has shut down, I want to take the time to enjoy hobbies and ‘playing’ with software, rather then rush into another great idea.

I’d like to do something that I

  • enjoy
  • have some form of domain knowledge of and contacts in already - so hobby related sounds like a start.
  • requires a sustainable amount of time and effort to build and maintain.

Like Andy’s strategy for products, I’m more interested in solving a few problems for myself first - if I enjoy it and people ask about it - then I might sell productized versions of it. For me - it needs to be a sustainable venture as I’m pretty wary of burn out these days.


I think you make a good point about the BIG difference in running a project as a hobby v running as a business.

Just some examples

  • Interested in trying out a new technology / technique? If you’re coming at it from a business mindset likely no - keep to proven tech and what you already know to keep dev fast and costs down.
  • Can’t be bothered with admin/writing manual/support - no probem as long as you won’t get discouraged by less people using it than they would
  • Want to try out something that interests you even if there is likely little chance of a successful business?
    etc. etc.

I’ve done a few side projects myself for exactly these reasons - helps keep me sane as the ‘day job’ (my own bootstrapped business) keeps me somewhat constrained.

After listening to the Stacking the Bricks podcast a bunch, I’ve decided to try building an audience of freelance programmers. Perhaps I’ll sell them an e-book on how to find clients. I don’t know if this is a good idea but in any case it won’t be time down the drain because I enjoy helping my fellow freelancers anyway.

Suppose you did build it (tho you’d have to compete with Brannan Dunn).

What’s next?

What are you going to sell to those people? A book? Doesn’t sound worth the effort.

Brennan pulls them into Planscope, where LTV is large.

Amy Hoy herself has a time tracking software. LTV is large.

But book alone, and not as a hook to something bigger, doesn’t make much sense to me.

I’d want to do it in such a way that I wouldn’t be competing head-on with Brennan Dunn. I came to know Brennan as the “double your freelancing rate” guy. I think he’s wanting to be seen in a little bit broader of a way now. In any case I’d want to pick some narrower area of freelancing, like building your professional network (probably bad example but you get the idea).

I imagine that if I can sell some freelancers a $39 book (for example), I can sell some of those book purchasers a, say, $199 course. Perhaps I could have some some of paid membership community. I’m really not terribly sure what would be next, to be honest. What I do know is that I’ve gotten some positive feedback in this endeavor so far, in the form of positive comments and people signing up for my email list, so for now it’s at least enjoyable and hopefully good practice making something people actually want.

Brannan sold some volume of his courses and materials. I believe he even published the numbers. So the path seems feasible.

But Brannan has created and ran a very successful (at least, by his words) consulting agency. Hence he has a trust that helps to sell such courses.

Do you have any special success in finding clients or other related activity?

If not, then it would be hard to match Brennan’s success.

And then again, Brannan is not just selling his courses, but nudge followers to use Planscope. Courses alone may not be too profitable (at least for him).

What I’m saying I guess is: it is worth to consider a long-term plan, with expected revenue, and do a reality check.

I’d like to remind that the goal is to get into that intersection of “you like and people want, and ready to pay for”.