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If you have the entrepreneurial itch and don't have the financial security to back it up, becoming a bootstrapped micropreneur is a great first choice.

Start your business on the side, when it revenue is high enough to live on, make the jump. It's slower than a funded startup, but a lot less risky. Does come with a high social opportunity cost due to lack of time, however. But so does starting a startup.

If your sidehustle does well, you can even leverage it later to fund your big startup idea. Or, hell, live a good life on a lifestyle business making a few hundred thousand per year.

$150k/year revenue won't get you any headlines, but it's plenty to live on and run a solo business.

Get to $500k/year and you prob have a higher expected ROI over N years than any startup founder.

Disclaimer: my sidehustle is at the $50k/year level, but that's on 60 hours per month. If I didn't insist on living in SF, I could have a very cushy life back in Europe.

Thanks for sharing. I find stories like yours more inspiring and motivating than the "ramen to unicorn" ones. I have little interest in scaling a business to IPO, but I'm very interested in building something that holds my interest and lets me support my family and an enjoyable lifestyle.

I totally agree with this - starting by bootstrapping is a great way to get your feet wet while maintaining a stable salary

Checked out your profile, is your side hustle a combination of books and teaching or do you have another product?

A combination of books and teaching. I'm experimenting with coaching and a company is sponsoring my React Native writing on a cobranded blog/yt channel.

I publish monthly breakdowns on swizec.com and that lists all revenue streams.

Did you leverage a mentor to get started on running something on the side? If so, where did you find one?

I never had an official mentor, but plenty of people helped and nudged me in the right direction and answered questions. You can find most of them on the internets.

It all boils down to this: Make things. Add "Pay For Thing" button. Tell people.

I started with following Ramit Sethi's emails for a few years (he's great to drive home the point that yes you do deserve to get paid), then Brennan Dunn's emails and content (he's great for "you totes can make shitloads"), then Nathan Barry's book Authority which is great for "Here are concrete steps to start making bank", and I went to Dunn's DYFConf which is like a baby MicroConf (to which I want to, but haven't, go), oh and of course I listened to all mp3s of all past talks from MicroConf. Patio11's writings helped a lot as well. I used Bryan Harris stuff for ideas on growing an audience, and Kai Davis is great for being a cheerleader and giving good ideas on positioning and writing.

Somehow I got invited to the Slack group where many of these micropreneur/microconf celebrities hang out and that's been superb as well. A lot of inspiration and great ideas.

Oh and I used Ken Wallace's MastermindJam to join a mastermind of likeminded peers. That helps with keeping you accountable and actually shipping stuff.

I also used Amy Hoy's 30x500, but I bought that too late (or too early, hard to say) and it didn't help super much. I should revisit.

Oh and levelsio's twitter stream is just a huge bundle of inspiration.

Thanks for taking the time to write this up. Plenty to look into.

I get the sinking feeling that achieving many of these things requires being charismatic and/or attractive and/or extroverted, of which I am none. Of course my marketable skill is not in communication but rather in engineering, so hopefully that won't matter.

I get the sinking feeling that achieving many of these things requires being charismatic and/or attractive and/or extroverted, of which I am none.

This has not been my experience of running a software company and, while speaking for others is always risky, most of the people mentioned in that list are personal friends of mine and I think would react to "good thing you are attractive and extroverted" with gales of laughter.

I'd argue that if you're thinking in these terms, you're probably not the startup type.

There was an interesting RibbonFarm essay on "guardian" vs. "commerce" syndrome that really crystallized this for me:

https://www.ribbonfarm.com/2014/06/04/saints-and-traders-the...

Entrepreneurs are the ultimate in "commerce" types, but beyond that, his key point was about bulletpoint #2, "exert prowess" vs. "compete". For most people, the point of effort is to get a reward; you are doing things now so that you can be the person you want to be at the end. You do your homework so you can graduate from a good college; you get a job so you can make money and live a good life; you get your MBA so you can get a promotion.

For a small minority of people, this is reversed. Who you want to be is just a guidepost for what you should be doing. It's the doing that's the important part. The RibbonFarm article describes this as the finite vs. the infinite game; guardian types do things for the victory at the end, while commerce types set the victory conditions so they have a motive to keep doing things. So you went to school because the material was interesting, and graduation was a little side-note along the way. Or you program computers because that's what you want to do, and the salary just determines who you should program computers for.

It's these folks who make the best entrepreneurs, simply because if you're playing to win, there are ways to win with less effort.

This, BTW, is why so many entrepreneurs go on to found repeat companies, and why a few are (frankly) dicks after they've gotten rich. A lot of folks can't imagine founding a company after you already have F-U money; why put yourself through all those challenges if you don't have to? But for many entrepreneurs, the challenges are the point, the competition is the point, and they don't stop competing just because they've gotten rich. Sometimes this is expressed in healthy ways, like YCombinator after ViaWeb, Medium after Twitter after Blogger, git after Linux, Stripe after Auctomatic, etc. And sometimes it's expressed in unhealthy ways, like Khosla's feud with San Mateo county over his beachfront property. But the point is that these people aren't founding companies because they need money or success, it's because they love the thrill of competition.

Sure. This is a nice dichotomy.

Until you add "living out of a car with your pregnant wife and 2 year old child" to the things you have organized your life to do.

Humans are very adverse to ruin, and this has nothing to do with what they want to do or achieve. It has to do with what they do not want to experience or put others through.

At some point we have to stop using "the wife" as an excuse. I can't tell you how many times a friend has used "the wife" as an excuse for...

not starting a project, not finishing a project, not learning something new, not starting a lifestyle business, not investing, not changing their career, not leaving a sucky job

It's not the wife, it's you.

If my husband risked our financials to the point that our 2 years old have to live in car while I am pregnant, the hell I would object. Financial misfortune or unemployment or not having choice is one thing, being irresponsible to that level just because you want to "feel like special doer" quite another.

Sometimes it is not the wife, sometimes it is the wife. And other times it is being responsible and considering consequences of your actions on your children before taking action.

This. My partner has no problem supporting me and I her; but we work together. And we don't take stupid risks just so that I can feel the thrill of competition.

I compete at my job -- I compete with myself to do better, to improve the company against all the challenges set before me, to provide more for my family.

There's nothing special about being an entrepreneur other than the privilege and ability to take serious financial risks.

This comment swings way too far in the other direction-- of course there is more to being an entrepreneur than privilege. That might help give you a chance at success, but it doesn't come remotely close to making that success a reality!

Unsuccessful entrepreneur is still an entrepreneur. Somehow the image of entrepreneurs tend to be someone who succeeded in the end, but plenty did not and they should count too - whether the cause was own mistake or bad luck.

I agree that there are also entrepreneurs that are not privileged and basically can afford risks because it can not get worst. And also enterpreners that don't take unreasonable financial risks - if you know you can get well paid job whenever you want to (as a coder or in friends/familly company) then it is less of risk.

Nevertheless, an original attempt to label responsible decision making as "excuse" and stigmatize it in favour of "following passion" or proving whatever to yourself or other emotions based decision was misguided. I don't know why some people treat it as decision you are supposed to make no matter what circumstances and skills. If they are really naturally ok with it, they should not need others to make the same decision.

People do definitely use their spouses and children to avoid taking on risks, but the fallout from a failed start-up can be devastating and many parents would (very reasonably) wish to shield their kids from that kind of instability. Especially if you're not in a financially secure place to begin with.

It's tough to suss out when a person is or isn't be too risk-adverse in general though. It may be impossible, in fact.

I find this unnecessarily aggressive and dismissive of people's (willfully chosen) social responsibilities. Yes, "the wife" is a convenient excuse for many things, including why you can't go out drinking tonight, even though you're really just tired from work and don't want to admit it. But presumably, if you're a decent person who has chosen to marry in this day and age, you take that choice seriously and choose your risks carefully.

I kind of see the point you are making, that some people don't do things that are good for them because they let their wife says no.

That said, I think you miss the point ABCLAW is making. A lot of people care highly about making sure that their family is taken care. This keeps them from risking everything on starting on a start-up.

As an aside, I see the options as 1) find a 8-5 I enjoy, get paid well enough to support my family and enjoy the extra time with them. 2) Start a company, work 80+ hours a week for >2 years for a <5% chance to never have to work again.

For me and my family 1 is a much more appealing option

>> it's not the wife, it's you

Also, anyone who thinks "I couldn't/didn't/wouldn't because ... " and hides behind those excuses, should read Charles-Bukowski's air-and-light-and-time-and-space (https://www.brainpickings.org/2013/10/04/charles-bukowski-ai...)

ZenPencils on air-and-light-and-time-and-space, for a more delightful read. (https://i0.wp.com/www.brainpickings.org/wp-content/uploads/2...)

This. If other people asked you whether you can start a project or not, and you reply using "wife" as an excuse, accept it for what it is. An excuse. I had met entrepreneur types that replied either yes or no, straight forward and no detour replies.

I did my startup while taking care of my parents and briefly paying ourselves very little. It sounded illogical to a lot of people. One of my friends honestly asked me if I'm doing the startup because I couldn't find a regular job (???). After a nice exit a large part of me is still itching to try again.

While living out of my car is a bit more hardship than I'm willing to endure or put my wife through, I do know people who have voluntarily quit their job and lived out of their car for six months or so, because seeing the country, rock climbing, and camping by the side of the road was more important to them. Heck, my wife lived in a house with 3.5 walls for 2 years (Peace Corps).

Hopefully you are not giving up things that are really important to you for the sake of pursuing your one burning passion. But there is a wide variance in the set of things that people consider important, much wider than contemporary culture considers. You don't have to choose the same goals that everybody else does, nor do you even need to choose a goal at all. Some people just live for the experience.

Sure.

When you're financially secure, it isn't a big deal to live out of your car and climb a few mountains for shits and giggles.

But what does that have to do, prescriptively, with the reverse situation, when you aren't financially secure? Very little.

Person in question wasn't exactly financially secure...I think he had about a grand or two in the bank, if that.

I think what commenters here are trying to drive home is that people have different "set points" about what acceptable risk tolerance is, and that we build up these ideas in our head of "I could never do X or live through X". But then if X happens, and we are experiencing it in the moment, suddenly the human brain has a way of adapting, most of the time. The important thing becomes that we are still alive, and we can still make choices, and then all the other strictures we set for ourself fall away.

Now, does that mean I suddenly want to go homeless, or have a grand in net assets, or live in a house where they didn't bother to finish all the walls, or try to build a startup while my kid is in the NICU? No. But by putting these options on the table, instead of making them no-go zones, you can consider them rationally and evaluate the likely probability of them happening, and then deal with them if & when they come up.

But she didn't understand
She just smiled and held my hand
Rent a flat above a shop
Cut your hair and get a job
Smoke some fags and play some pool
Pretend you never went to school
But still you'll never get it right
'Cause when you're laid in bed at night
Watching roaches climb the wall

If you called your Dad he could stop it all

Have you heard the Shatner cover of this song? It's pretty great.

>Person in question wasn't exactly financially secure...I think he had about a grand or two in the bank, if that.

That's quite a bit more than the average person has. Especially if you're a coder and can land a 175k/yr job by sneezing at linkedin.

I understand what commentators are trying to do, but the attempt is misguided. I'm replying to a post regarding a dichotomy between being and doing as the foundation of entrepreneurship, and I've stated that this simply isn't the case. The risk-tolerance of a prospective entrepreneur has nothing to do with how their self-perception of reward is set up.

It has to do with how robust they are against the chance of ruin. When ruin isn't in your calculations because your parents or friends have a spare couch to crash on and you don't have a sick newborn to take care of, you discount its importance in dissuading people from having your same risk appetite.

Very seductive mindset, too, as it lets you ascribe a prescriptive virtue to your choices: "If only people were as daring as me!"

I've lived in my car to start a company. I've also failed with a one month old baby in the NICU. It's not the end of the world. You can always go back to having a job.

On the flip side, people who are dependent on the good graces of increasingly deteriorating established socialized methods of making a living probably shouldn't be having children either. A lot of people who don't work in startups find themselves in that position too after layoffs and etc.

> Don't start a startup if you have family that depends on your income.

This one deserves to be called out. You can make a perfectly respectable living starting a company (perhaps not saving as much), and if it doesn't work out and you're savvy you'll have a job in no-time. Especially if you're an engineer in the bay area.

This is indeed true, but your family might suffer from what you're ready to give away when they are not. This is what I experience right now and it's not always easy.

I agree with most of what you wrote, but I will say that people outside of the scene might not realize how common it is for founders to raise a couple million in seed funding, then pay themselves a market salary (I've seen as high as $350K for a CEO of a ~10 person company), removing most of the downside.

I'm not saying this is advisable, but it's common.

On the flip side - if you want to be a founder - try to start early. On balance you often have fewer constraints, lower expenses, and much more life flexibility.

Or start later because you are likely to have higher savings, better contacts and more experience.

Starting later selects for a founding a different kind of company than the one a fresh graduate/drop out would found.

I don't think there is a best time to be a founder; it's largely an individual thing.

The odds of there being an exit worth anything to anyone other than a founder are small enough to not even worth considering.

So if you go to work for a startup, you should demand substantially more money than with an established company.

It didn't used to be that way. It used to be that the first dozen or so employees of a successful startup did very well, and the first hundred or so did OK.

> So if you go to work for a startup, you should demand substantially more money than with an established company.

The problem is that most startups can't match, much less beat, established companies on salary, and they'll just turn you down. It's not even malice or greed on their part, it's just that they have a finite runway and a few tens of thousands of dollars a year on a single person can mean the difference between life and death.

No one wants to say it out loud, but I'm starting to think that the startup economy requires people to accept the gamble of shit salary for a chance at the equity lottery. I decided not to play along with that and only work for megacorps, but it's up to each individual.

The megacorp economy requires people to accept the likelihood of crushing institutionalized misery in exchange for a chance at being able to sustain a high salary long enough that the accumulated pile of cash after you finally quit will allow you to live a good enough life to make up for all that lost time and deferred happiness. I decided not to play along with that and will never again work for a megacorp, because life is short and I want to enjoy mine. It is, as you say, up to each individual!

But then you have kids, and kids require stability. So you go to work for the man, because the kids are more important.

But... start ups still pay engineers salaries that dwarf teachers, retail, and many other industries. Should people in those industries not have kids? Are they being irresponsible by not making 6 figures?

I wasn't talking about money, I was talking about stability.

People working in software field are extraordinary and deserve extraordinary perks is held as self-evident truth in modern world.

Actually, I don't think many people can stop that "institutionalised misery" spilling out into their family life.

Exactly, be miserable so the next generation can do it too! People raise children in total poverty all the time dude, I'm sure you're going to be fine.

> No one wants to say it out loud, but I'm starting to think that the startup economy requires people to accept the gamble of shit salary for a chance at the equity lottery.

Eh, lots of people say exactly this out loud. People who accept that gamble jsut like to pretend their chances are higher than they are and/or it's worth it for the work experience.

There's more to it than the small chance of winning the equity lottery. Working for a startup confers a number of non-monetary benefits that mega-corps don't. If you pay a startup-salary and then stick people in a cubicle and have them write TPS reports and deal with petty politics (ie: mega-corp conditions), people won't work for you.

The feeling of working for a company that will make a dent in the world, so to speak, and that your effort will have tangibly supported creation of said dent is a powerful motivator.

The odds of "making a dent in the world" are pathetically, abysmally, absurdly small. You cannot plan for that. It just happens to some people and that's it.

If by, so to speak, you mean that some dents are bigger than others -- sure... contributing to a small startup that makes some people a decent amount of money and the rest practically nothing... sounds great. Turns out the bigger the exit the less the rest of the people make and the more a small group of people do. Of all the companies big and small that are started around the globe each day, how many have "made a dent in the world?"

It may as well be zero.

If you cannot be motivated internally you're not going to find it very satisfying to continue taking risks working for (or starting) startups. When the first one fails, and the next few, and you never end up making that dent... you're going to be very disappointed.

You can use that same internal motivation at a big-corp as you can working for a start up. Or anywhere else in life.

Yeah that's not gonna happen. Startups are lots of work for low pay, with the lottery ticket that you might be the 1% who makes it out.

You ask for a megacorp salary and you'll be laughed out the door.

How exactly are startups supposed to get the best engineers without paying market rate for labour? Given the emphasis on only hiring rock stars, you would think that startups would offer higher salaries than megacorps. Relying on your prospective employee being too dumb to notice the raw deal that she is getting is not a recipe for hiring good employees.

Work and growth opportunities, the promise of being paid out if it succeeds. At a startup you can play with the latest hot technologies and if the startup is growing fast enough you can accelerate your career into positions faster than a large corporation.

Being a successful business is not all gambling luck, it's not always working long hours for crap pay, and many, many people have started companies with families and without losing everything they put in. Also, "90% of people choose not to work at a startup" seems like a really bad guess.

I didn't suggest it was impossible or that you couldn't start a business when you have a family or other dependents. I do believe that it's risk to start one or work at one if you do not have ways of mitigating the risk to the people you are responsible to.

It is fundamentally a gamble. Everything else is risk mitigation: having a savings account with enough money to cover your obligations of for a couple of years, starting in a low-risk niche, working with partners, insurance, etc, etc. In the end the market may make the venture a flop: hopefully you've taken enough precautions that it doesn't leave you with a foreclosed house and filing for bankruptcy.

The only real competitor anyone should care about is themselves. Being an entrepreneur, recklessly, is not going to satisfy that itch in the long run.

true but the odds are getting better..it use to be 20%, it's now at 30% contrast that to small biz is now at 50%

Where did you get that 30% figure, if I may ask? The usually cited figure is 10%.

> The usually cited figure is 10%.

Right. And even that 10% is very optimistic. It's closer to 5% or 7% at the most.

> This number suggests that a startling 93% of the companies that get accepted by Y Combinator eventually fail.

Source: [2013] "DEAR ENTREPRENEURS: Here's How Bad Your Odds Of Success Are" => http://www.businessinsider.com/startup-odds-of-success-2013-...

I second this request.