> I’d go so far as to say most entrepreneurial challenges that we hear being bemoaned are a direct result of your chosen path being incompatible with your business idea or life circumstances.
This! It seems that the loudest story being told is about the 18h work day, silicon valley VC, elevator pitch, market-fit, exit strategy.
But that is not the only story, the others seems barely told... (except in a few HN threads)
- I do apps for businesses on the Atlassian Marketplace,
- First year was 3000€ (the whole year),
- Year 3 went over the engineer salary quite easily (we’re now a few employees and we gross ~200k€ for each worker).
- I’m a pretty hard worker, but I don’t believe I go over 40hrs/week in average if you count errands we run "exceptionally" the day (walks, meeting friends, etc) + 4 weeks holidays. Weekends may be at work, but I’m then less focussed during the week, so it evens out.
So it has been pretty easy bootstrapping. Of course life is hard, but it is hard for other jobs too.
I think the entrepreneurs’ biggest force is normal companies spend 50% of their workforce synchronizing with colleagues...
That comment was just to show there are happy stories. Big thanks to HN and especially Kalzumeus for teaching me how to do business. I’m forever indebted but, being extremely bitter with life, I’m currently bad at reimbursing. Currently. I still teach my experience to every school I can, though (but with more talks about the downsides of course).
I was a fan of their products first; Once I was in a gig at a customer’s office (standard Java/Spring $350, nothing fancy) and I identify a typical problem that all companies have (Don’t really want to tell you, because I’ve said on this forum I vote Trump so I don’t want people to retaliate against my product) and I thought the best place to implement it would be a corporate tool, like the Atlassian products. Long story short, it really took employees a lot of time to do a task, « which I can automate in 2 days as a programmer » (that’s what every programmer says before they spend a year on it).
I finished the gig then I developed the solution alone, and indeed there was decent demand for it. And once it was well-designed, there was even more demand for it. And when we marketed for multi-node clusters... it seems we could charge anything we want as long as we have the enterprise features (cluster, performance reports, XML export, REST APIs, permissions, all those details that are important for companies).
> The psychological toll of not feeling like you’re “all-in”
I'm bootstrapping my own SaaS solo and this one hit real close to home. I've been at it for a couple of years, and as of Feb this year it became a nights/weekends project as I had a great opportunity for a full time job that I couldn't pass up.
Life definitely gets in the way and makes me feel like I'm not working hard enough, but it's a hard balancing act with a full time job. Plus having a wife who's pregnant with twins (our first kids), so just another wrench thrown in there!
A tool for mortgage loan officers (or anyone who actually runs the numbers) to automate creating accurate estimates. It started out as just a tool to save myself time that I built more onto over time.
It makes money, and my "worst case" scenario of it helping to land me another job through personal growth played out. I'm still pushing it along, but it's a struggle at times.
> While I understand that no one wants to wait a few hours for a response to their question, if you’re bootstrapping with a small team you’re likely not going to be available 24 hours per day.
In my experience, customers who sign up, demand immediate customer support, then cancel a few hours later because they didn't get it, are doing you a favor - imagine what a drag on your customer support efforts they'd be if they stayed!
My rule of thumb is customer support thru email should aim for 24h turnaround, except if they're paying for "premium support". Great if you answer in 5min because you were just at the helm, but you shouldn't set unreasonable expectations.
Live support is murkier - if you do have set it up and are offline, falling back to email that gets answered tomorrow does seem slow, just by the fact you've just anchored me to "live". In my opinion, don't do it (or hide the widget!) unless you can really provide near-realtime response (even if via outsourced 1st level support agents).
I disagree. When you’re starting out, support is one of your key differentiating features. Customers will love you and stick with you because you’re there to help them when they need it.
Those conversations, beyond just delighting your customers, are where you really learn the most about them and their needs. It’s where you get to live their pain and understand what you can do to build a better product. I’d recommend being ready to jump on the phone with someone the moment they reach out for help.
Also, you can be honest about out of hours times - people understand that you can’t be there at 1am (though, lord knows I’ve done plenty of support with customers on the other side of the world at that time). But if you’re a tiny company getting established, you’ll be on hand at all hours, even if it’s a bit antisocial. Nobody is as loyal a customer as someone you’ve bent over backwards to help late at night or on a Sunday afternoon.
24 hours can make it hard to coordinate times to talk (maybe they were expecting you to call back that day but not the next one), but is still great service in my field. Responding within a few hours and in person is definitely going the extra mile and will win you fans.
> people understand that you can’t be there at 1am (though, lord knows I’ve done plenty of support with customers on the other side of the world at that time).
That is the most pleasure I take. Underpromising, yet answering tickets or taking a call at midnight. It happens once or twice a month. For the call, she told me she was stuck with a customer demo, in exchange I made clear that I wasn’t « in a work environment » and all went well.
Those customers seem to get emotionally attached to us. In fact, they’re the only kind who give reviews on the Atlassian Marketplace (either those for positive reviews or the occasional disappointed person). They are a bit idealists though, and I don’t see them after two years, whereas corporate customers stay for much longer.
I completely agree that bending over backwards for users is a competitive advantage and customers won't forget it. But that does need to somehow reconcile with your availability and life outside of work—that's the rub for small bootstrapped companies.
I'm also in the camp of not offering live support. For most businesses who don't have a 24/7 staffing for the live chat, it's best to avoid it altogether as it creates unrealistic expectations in the customers.
Customers who require instant support at whatever hours will likely find some dissatisfaction in working with your bootstrapped solo founder company now or in the near future. Best to offload them to companies who are ready and structured to help them.
Support is the oxygen to the brain. Its a schlep if you dont like people in general but its the one time you can personally talk to someone who is validating your business.
I always see a potential relationship there and you know what? People reciprocate. I once got a call and the customer was telling me her company was unsubscribing. She didn't have to tell me. Can you imagine waking up and telling a Mailchimp that you are unsubscribing?
Long story short, support is one of the infinity stones. If you do nothing else --- do that!
> The hard truth that no one wants to give lip service is that early on, bootstrapping your company may be the best decision for you but it’s not the best decision for your customers.
I'm surprised this was highlighted in the article. It is one of the least compelling statements. VCs drive for high risk, fast growth plans, while what customers need is stability. If they have a service that works for them, at a solid price point, where the service meets their needs while delivering a profit for the business, then everyone wins. The last thing that a customer needs is for a working product to pivot into a high-growth plan that puts the business in the red in pursuit of even more profit.
That's a good point and I agree with what you said. But I think so many customers are accustomed to working with large, public or VC backed companies where response times are near immediate, product polish is higher, etc. When that's viewed as "the norm" then life becomes harder for bootstrappers.
> For me personally, this meant that for years, literally, there was always this nagging feeling that I could be doing more. I could be doing more or doing better for Outseta, and I could be doing more in terms of the other projects I was working on as well. For me, that feeling has been tough. It feels really good to be able to say that you unequivocally, without question, are giving something your all.
This has been the dealbreaker for me whenever I've tried to bootstrap side-projects or incubate potential startup ideas while holding a full-time job. It always leads to frustration after a month or two, since I'm unable to perform to the best of my abilities on either the day job or the side project.
For me personally, the better route (for my sanity, at least) has been to double down on my career, putting everything into the day job. The big downside of course is that I've had to put any startup plans on hold indefinitely. But the upside is that I only have to focus on one thing (day-job performance), and since I'm lucky enough to be in an organization where performance is rewarded, that has led to career progression over time.
Rather than inflate my lifestyle, I've continued to live modestly and save/invest my compensation bumps. This extends my personal runway and increases my confidence that when the time is right, I'll be able to responsibly quit and focus 100% on my own thing without risking my family's financial wellbeing.
I know this isn't the right path for everyone, but for me at least it's what has kept me sane!
This makes a ton of sense—far too few people reach this conclusion and realize that picking one path or another is a key to their sanity and happiness!
Choosing a ‘mission critical’ idea definitely ups the difficulty into hard mode. That’s number one on my list of ‘can’t have’ items for bootstrapped software because I just don’t want to deal with 24/7 instant support.
26 comments
[ 2.4 ms ] story [ 69.7 ms ] threadThis! It seems that the loudest story being told is about the 18h work day, silicon valley VC, elevator pitch, market-fit, exit strategy.
But that is not the only story, the others seems barely told... (except in a few HN threads)
- I do apps for businesses on the Atlassian Marketplace,
- First year was 3000€ (the whole year),
- Year 3 went over the engineer salary quite easily (we’re now a few employees and we gross ~200k€ for each worker).
- I’m a pretty hard worker, but I don’t believe I go over 40hrs/week in average if you count errands we run "exceptionally" the day (walks, meeting friends, etc) + 4 weeks holidays. Weekends may be at work, but I’m then less focussed during the week, so it evens out.
So it has been pretty easy bootstrapping. Of course life is hard, but it is hard for other jobs too.
I think the entrepreneurs’ biggest force is normal companies spend 50% of their workforce synchronizing with colleagues...
That comment was just to show there are happy stories. Big thanks to HN and especially Kalzumeus for teaching me how to do business. I’m forever indebted but, being extremely bitter with life, I’m currently bad at reimbursing. Currently. I still teach my experience to every school I can, though (but with more talks about the downsides of course).
I find that the hardest part for me is to figure out what to build and for whom
I finished the gig then I developed the solution alone, and indeed there was decent demand for it. And once it was well-designed, there was even more demand for it. And when we marketed for multi-node clusters... it seems we could charge anything we want as long as we have the enterprise features (cluster, performance reports, XML export, REST APIs, permissions, all those details that are important for companies).
It makes me think of a particular problem that I have fixed for a client quite a few times already that could be automated.
Good luck in your endeavors!
I'm bootstrapping my own SaaS solo and this one hit real close to home. I've been at it for a couple of years, and as of Feb this year it became a nights/weekends project as I had a great opportunity for a full time job that I couldn't pass up.
Life definitely gets in the way and makes me feel like I'm not working hard enough, but it's a hard balancing act with a full time job. Plus having a wife who's pregnant with twins (our first kids), so just another wrench thrown in there!
It makes money, and my "worst case" scenario of it helping to land me another job through personal growth played out. I'm still pushing it along, but it's a struggle at times.
In my experience, customers who sign up, demand immediate customer support, then cancel a few hours later because they didn't get it, are doing you a favor - imagine what a drag on your customer support efforts they'd be if they stayed!
My rule of thumb is customer support thru email should aim for 24h turnaround, except if they're paying for "premium support". Great if you answer in 5min because you were just at the helm, but you shouldn't set unreasonable expectations.
Live support is murkier - if you do have set it up and are offline, falling back to email that gets answered tomorrow does seem slow, just by the fact you've just anchored me to "live". In my opinion, don't do it (or hide the widget!) unless you can really provide near-realtime response (even if via outsourced 1st level support agents).
Those conversations, beyond just delighting your customers, are where you really learn the most about them and their needs. It’s where you get to live their pain and understand what you can do to build a better product. I’d recommend being ready to jump on the phone with someone the moment they reach out for help.
Also, you can be honest about out of hours times - people understand that you can’t be there at 1am (though, lord knows I’ve done plenty of support with customers on the other side of the world at that time). But if you’re a tiny company getting established, you’ll be on hand at all hours, even if it’s a bit antisocial. Nobody is as loyal a customer as someone you’ve bent over backwards to help late at night or on a Sunday afternoon.
That is the most pleasure I take. Underpromising, yet answering tickets or taking a call at midnight. It happens once or twice a month. For the call, she told me she was stuck with a customer demo, in exchange I made clear that I wasn’t « in a work environment » and all went well.
Those customers seem to get emotionally attached to us. In fact, they’re the only kind who give reviews on the Atlassian Marketplace (either those for positive reviews or the occasional disappointed person). They are a bit idealists though, and I don’t see them after two years, whereas corporate customers stay for much longer.
Customers who require instant support at whatever hours will likely find some dissatisfaction in working with your bootstrapped solo founder company now or in the near future. Best to offload them to companies who are ready and structured to help them.
I always see a potential relationship there and you know what? People reciprocate. I once got a call and the customer was telling me her company was unsubscribing. She didn't have to tell me. Can you imagine waking up and telling a Mailchimp that you are unsubscribing?
Long story short, support is one of the infinity stones. If you do nothing else --- do that!
I'm surprised this was highlighted in the article. It is one of the least compelling statements. VCs drive for high risk, fast growth plans, while what customers need is stability. If they have a service that works for them, at a solid price point, where the service meets their needs while delivering a profit for the business, then everyone wins. The last thing that a customer needs is for a working product to pivot into a high-growth plan that puts the business in the red in pursuit of even more profit.
This has been the dealbreaker for me whenever I've tried to bootstrap side-projects or incubate potential startup ideas while holding a full-time job. It always leads to frustration after a month or two, since I'm unable to perform to the best of my abilities on either the day job or the side project.
For me personally, the better route (for my sanity, at least) has been to double down on my career, putting everything into the day job. The big downside of course is that I've had to put any startup plans on hold indefinitely. But the upside is that I only have to focus on one thing (day-job performance), and since I'm lucky enough to be in an organization where performance is rewarded, that has led to career progression over time.
Rather than inflate my lifestyle, I've continued to live modestly and save/invest my compensation bumps. This extends my personal runway and increases my confidence that when the time is right, I'll be able to responsibly quit and focus 100% on my own thing without risking my family's financial wellbeing.
I know this isn't the right path for everyone, but for me at least it's what has kept me sane!