Ask YC: How to start becoming an entrepreneur while still being an employee

I realized my comment was too damn long, so I wrote a blog post.

http://www.tonywright.com/2008/half-assed-startup-how-to-sta...

Nice blog post, but I object to the "half-assed" phrase in the title, which implies a lack of passion for the startup. Sometimes, I think that one must keep a source of income out of necessity (and consulting is not always feasible).

I worked on my startup part-time for 9 months before taking the plunge and quitting my day job 5 months ago, and "half-assed" is pretty accurate, even if it is a little unpleasant. In terms of the scope of what you can accomplish, you're severely handicapped by moonlighting, much moreso than the difference in available time would suggest. Being able to think nearly continuously about your project lets you try much more ambitious projects, which you wouldn't be able to hold in your head otherwise.

One thing that helped me was to think of my salary as "buying time". If you make $60K but live on $20K, then each hour you work buys you two hours of startup time. If you make $100K but live on $40K, each hour you work buys you an hour and a half. Shows you how important it is to get your living expenses down.

Another thing that helps is to live like your least-successful classmates while working like your most-successful classmates. I have English-major friends who graduated, couldn't get a job, took a string of temp jobs and secretarial positions, spent as much time on unemployment as off, rarely had money to spend, and went back home to live with their parents. So, I went back home to live with my parents, rarely spent any money, and worked at a financial software startup. I pocket the difference between a Starbucks salary and a financial software salary. That's given me about 4 years living expenses to work with, even assuming I were to move out of my parents.

Nice "comment". Thanks for taking the time to pen it. Have you thought about extending RescueTime to offline activities? I know a lot of people who work remote and they've told me disclipine/habits are the key to working effectively when you lack the peer pressure environment of the typical office.

I think some of your previous comments (e.g. virality) could be turned into their own blog posts. I think throwing a comment out into the News.YC slipstream is a good way to see if you're writing yet another echo-chamber/me-too mini essay (which is probably what you don't want to do)

I've tried the "just do it" approach in the past and now believe its nonsense. Be calculating and methodical, not impetuous.

Do's/Dont's: Don't work on your stuff on employer time. Make sure you have energy left after work for your project (sometimes that means not being the star performer at the day job). I work my day job from 8-5, and my startup from 6-11 EVERY WEEKDAY. Weekends its ALL DAY developement. Have a product roadmap, release dates, and work your tail off to meet them. Do your architecture design work during the week at lunchtime (off site). Cut anything from your time that isnt helping you meet your goal (ie I dont even drink beer anymore because it hinders coding).

Read this for inspiration (its short): http://loiclemeur.com/english/2007/12/the-idea-does-n.html

Finally, only quit your day job when your startup is making your salary.

"... I've tried the "just do it" approach in the past and now believe its nonsense. Be calculating and methodical, not impetuous. ..."

Nice description of "project management" which seps boys from the men [0] and makes a difference in completing a project. Does it allow you to be flexible enough to adapt to experiment & change?

[0] Max Levichin talked more about this in StartupSchool '07 - (I think).

Err yeah sure that will work. My advice: read the four hour work week. Not for the four hours but for putting you in a position to work for yourself and work as an employee.

Focus obsessively on your productivity on your current job and take on no new tasks. Hopefully get your tasks done in 10 hours per week (very easy if you get rid of all possible meetings and phone calls). Use the extra time to work on your own startup.

If the extra time belongs to your employer, then so does the copyright on any work you do during that extra time. Don't write any programs, documentation or marketing literature on employer time. Do focus on productivity, though. You need to be in the habit of being productive.

During those work hours, you can do stuff like pay bills and make phone calls that would normally occupy your off hours. Optimize your off hours, at expense of your work hours.

It's probably wise to consult a lawyer about this, but for my part, I say go ahead and work on your employer's time. Understand that you are taking a calculated risk. If the risk (e.g. getting fired, losing ownership of your work) isn't worth it, don't do it. But if it is, then stay as productive as you were before at work while trying to be as efficient as possible (e.g. by using methods in the Four Hour Work Week) to squeeze out extra time for your project. On your own time, work as hard as you can without skimping on your other obligations (e.g. family, bills, etc.).

I believe California has a specific law that whatever you do for yourself is your own property, in regards to IP. I assume other states have similar laws on the books, but it isn't universal.

<disclaimer>I'm still in the process of starting my first business and still working for 'the man.' Take what I say with that in mind.</disclaimer>

I've mulled over this question a lot. After reading all kinds of articles and books about founding a business, it seems to me that the key to becoming an entrepreneur is "just do it." Nothing will teach you more about being one than actually doing it. There is tons of GREAT advice out there but none of it will actually become applicable until you're put in a situation where you need to apply it.

Finish your app, start the business on the side, and see where that takes you. Nothing like market forces to expand your comfort zone for you. If your business starts taking so much effort and time to iterate that you need to decide between your job and your business, take it as a good sign. If it fails, so what? Almost all the big name founders had at least 1 failed businesses before hitting gold-some of them had multiple failed businesses.

Personally I've never been able to really combine work with startups. You are single-threaded, so to speak, so doing things sequentially (work -> quit -> start company) works better than multi-tasking. Plus, staying on the job gives you too much comfort. Here are four things that I have done or considered doing:

1) Try to sell your startup idea to management. Chances are it won't work, but it's worth a try - the company might invest money or people in it. This one actually never worked for me.

2) Try to steer your work at the job so it overlaps with your startup. E.g., if you think your startup should use Python, but you don't know it, persuade your boss to use Python for your next work project, so you can get the hang of it. Persuade your company to open source some code that could help you for your startup.

3) If you work in a place with good bonuses (50%+ of annual salary), work hard, wait for the bonus and quit. That's what I planned to do, but my hedge fund went bankrupt three months before bonus time. Still, I got a decent settlement, so it worked even better.

4) Decide you are quitting, but don't announce it. Become a bad employee. Note that this is immoral, dangerous and potentially illegal, plus faith has its way to play jokes on you, so after you burn the bridges with your boss you might meet her again in a different scenario (e.g., she becomes a VC). Leave the office earlier, start working from home more often (while actually working on your startup), try to take a 1-2 month vacation/sabbatical, etc. Unless you work at a 7-11, you would usually have 2-3 months before management starts coming down on you. This way you can work on a prototype and if two months in you realize it's not worth it, you can still recover things at the job.

Already working on #1 and #2. In alignment with some others, trying to sell a project that would be perfect with Ruby on Rails to the powers-that-matter. I think #3 and #4 aren't in my nature.

"act more like an entrepreneur at your current job. Be a maverick. Put in longer hours, give yourself a crash course on your company’s operations and strategic goals and, most important, locate a problem outside your realm of expertise and solve it."

I think this is more reflective of someone looking for growth, than an entrepreneur, and I say that to say this: standing out from the crowd and working like you're worth they money they're paying you will most certainly bring you the kind of attention outstanding entrepreneurs get and you may just get a promotion out of it

However showing the spirit of someone who is supposed to start things should mirror actions that look like you're wanting to start something. Make suggestions, present solutions like the second half of the quote says to, but in addition to this build momentum behind your ideas and show why they matter and how they'll make improvements.

Just start working on your startup when you're not at work. The extended work hours and work load will get you ready for when you make the full transition.

I'm not sure they recall that I'm the same guy, but I sent an email to YC 16 months ago that I'm almost embarrassed by. I asked how to take action on good ideas while staying at a job I loved at a company likely uninterested in the ideas.

If I could go back to myself 16 months ago, I'd say: "Grow a pair and do what you want, and only that -- ohh, and short the home mortgage industry"

It's all about the focus.

Like drunk dialing, sometimes sending embarassing emails help remind you that you've improved.

When did you reach the tipping point (was it a group or individual decision) with Tipjoy?

The best quote about focus that I've ever heard: A 100 watt lightbulb can light up a room but that same energy focused in a laser apparatus can cut through steel.

Talking about Tipjoy is what made my cofounder (also my wife) and I decide to go for it. She was at iRobot. I was at Nokia. Both of us had excellent jobs.

The clincher that made us quit was when it became perfectly clear that those jobs, or their equivalent, are readily available should we fail. If the worst, worst case scenario is the status quo, why not go for it?

"... how do you go about making the transition to full-time entrepreneur ..."

Make stuff [0], release early, get some feedback and sell it.

It doesn't have to be software but it helps. If you make things nobody wants you quickly find you can't sell it. You have to listen & adapt. It's much like a multi-levered machine that only stays afloat if you are constantly adjusting the levers finely adjusting the final product according to users. Input product, make sure people know about it, adjust the 'want' lever. Listen to what the machine is telling you. Adapt.

This process can be observed from renovating houses, art ... from sausages to software. It is no substitute for the real thing. So burn your boats now.

[0] Stuff could be sausages, software etc, but make sure that it's product not service or skills for hire ~ http://www.joelonsoftware.com/articles/FiveWorlds.html

Assuming it is a web startup.

Build a content website on something you consider yourself good at. Try to get users, make money through adsense, put up analytics and test it out. You would learn a ton about how(and what) works on the internet - and possibly be making enough by the time you are ready to quit to bootstrap your startup .

Well, I've started a stationery shop in my cube...

Seriously, though, I think one way would be to become more entrepenurial at work, and try and apply some of the kind of fairly ruthless behavior that I'd imagine you'd need to survive in a startup.

In no particular order: Focus. Get Things Done. No Fluff. Delight Customers. Play Necessary Politics.

Another way to think of this, might be to look at all the employees that, in a start-up environment, would sink like lead bricks, and do exactly the opposite.

Your first lesson as an entrepreneur:

Your last paragraph is exactly what NOT to do. You will need every single ounce of resources (time, energy, attention) for your start-up. The only reason to ever do anything above the call of duty as someone else's employee is to learn it for yourself.

Start your planning on how you will extract yourself from your current employment, going part time or as a contractor. You will need every spare nanosecond for your startup.

And don't sign anything. (If you already did, get a risk assessment from a lawyer.)