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Ask HN: Oops, I just sold my startup to a piano company. Now what?

151 points by dangrover ↗ HN
So the last time I relied on you for advice was 1394 days ago, according to this: http://news.ycombinator.org/item?id=134685

Since then, I worked at a few startups, dropped out of school, started a successful Mac app business, and ended up spinning off a music publishing platform for the iPad that was doing very well until I ran into a legal issue.

So I exited earlier than I would have liked:

http://steinway.com/news/press-releases/steinway-sons-debuts-etude-20-ipad-app-for-learning-and-playing-piano/

The heart of the matter was that I signed a bad contract with someone who was supposed to get music deals for me. With the contract in place, it limited my options for continuing to bootstrap, taking funding, or getting acquired by a few of the companies I was talking with. Except for Steinway, which found a way to work with me.

So I moved from SF to New York, I brought in a team, we transitioned the app over, built one of the first sheet music stores for the iPad, and released a new version of the app I'm really happy with.

If you're curious, you can try it for free at: http://etudeapp.com

With the app transitioned and my legal matter finally settled, we've set a date for me to leave the company. I'm excited, but a little terrified.

Since the time I sold, I have many times the resources/runway I had before, and I'm a good deal more mature and in much better shape. The odds are waaay better, so I ought to just hang out and see what I come up with, right?

But for whatever reason, after spending about 2-3 years pursuing a single idea so passionately, I'm pretty burned out, and I'm not quite ready to start something new yet. I'm not excited about any of my other ideas to the degree I was with Etude, and I'm having trouble seeing what to do now. I feel like I've reached a local maximum, and I need to go work with other people and see what kind of ideas they're into.

I'd really like to do an incubator like YC, since having decent advisors would have prevented me from running into the trouble I did before. But it's not the right time, and I'm (so far) a single founder.

So I went and interviewed at a bunch of places in New York (since I'm stuck for at least a little while). People seemed to like what I'd done and I got a few offers from some good companies, traditional and startup.

I don't really need a gig, but I figured I'd see what I could get. But the thing that bugs me about this is that nobody seems to think that I'm anything more than a code monkey. They don't realize that, in addition to engineering, I actually started something new, managed the product, a whole team, did a fair bit of design, promotion/press, successfully exited, all sorts of stuff that doesn't really fall under "Objective-C developer." Not exactly covered in the Stanford course. I'm not usually so arrogant, but it's frustrating.

For some reason, the logic on the east coast, and even in a lot of SV is, "If you can code, then you can only code. Forever."

I'm returning to San Francisco for a week just to meet up with some old friends and escape the cold later this month. Hoping that will help me.

But what should a person who wants to take a break and get some broader experience but is tainted with an engineering background do? Is the only option for me to just suck it up, gather the courage, and commit to striking it on my own with another idea? Have any of you ever been at a similar crossroads after exiting something?

75 comments

[ 4.5 ms ] story [ 171 ms ] thread
aaronwhite
If you don't need the money, take time off. When I left the last startup I co-founded, I decided to set an arbitrary "1 whole year" date, during which time I would explore my own projects, hear about other peoples new ideas, and talk to existing larger startups (Dropbox, etc). But I wouldn't allow myself to commit to anything until about a year was over. It's too easy to be come enamored w/ half-baked ideas, and I wanted to make sure the next one was meaningful and had a high probability of success. Long story short, I learned a ton during that year, turned down some great options, and eventually chose the BEST of all possible options. (Starting a meaningful company w/ killer co-founders, gaining traction, and having a blast)

If you have the chance, give yourself the space! It'll be worth it.

keiferski
Read the classics. Learn how to paint/draw/sculpt. Travel to random places. Keep a journal on what you want to do with your future.

After a few years of the above, you should have a much better idea as to what you want. Jumping from one intense startup to another (or into a random job) won't give you time to sit back and reflect.

roobeast
Take a year and go travel. Set aside an amount for a healthy runway when you return, then you will have better clarity if you want to start something new or go work on someone else's idea. There are many companies that segment the workforce into "can code" and mba/product people. Try not to work for one of those places. You can find someplace that values both skills in an individual however it may take a while.
jey
> But the thing that bugs me about this is that nobody seems to think that I'm anything more than a code monkey. They don't realize that, in addition to engineering, I actually started something new, managed the product, a whole team, did a fair bit of design, promotion/press, successfully exited, all sorts of stuff that doesn't really fall under "Objective-C developer." Not exactly covered in the Stanford course. I'm not usually so arrogant, but it's frustrating.

Do you market yourself that way? You have to tell people what they're supposed to see you as, and then they'll decide whether it's true or if you're just pulling their leg.

That said, I agree with the other posters and think you should definitely take a break and allow yourself to drift into the next big thing.

dangrover
That's a good point. If there were some openings for "startup douche", I'd apply to those. I think I'd be very qualified. :)
jey
Forgive me for playing psychologist, but I'm detecting a bit of insecurity. You should internalize that you really are awesome & rare, as evidenced by the fact that you single-handedly created a high-quality product and sold it.

Examples:

> I'm (so far) a single founder.

Doesn't matter, you have a great track record. Yes, it's better to have a good team, so you should keep an eye out for teammates.

> nobody seems to think that I'm anything more than a code monkey

Sounds like maybe you haven't presented yourself as more than that to them.

> If there were some openings for "startup douche", I'd probably apply to those.

What's douchey about winning?

bryanh
If you have the runway, bum around. Take the time and enjoy it. Work on what interests you. And don't let yourself be jerked around by some false "engineering background" stigma, you are clearly a kick ass hacker. Hack away. Good things will come (again).
yan
Dan, I remember seeing your story those 1394 days ago (only to join a few days later) and it's amazing to see what you've accomplished.

I've been working on trying to get out and do other interesting things around that aren't tech-related, mostly outdoor and alpine-related. NY area isn't exactly the outdoor paradise that some other places are, but I'm working on getting some like-minded people together to get away from the glare of displays. Get in touch with me if you're interested.

edit: If anyone else is interested, please feel free to get in touch.

chernevik
NYC has outdoor opportunities, but they require car range of about 4-6 hours and some planning. Tough for people with families, but you kids go have fun.

White Mountains -- are only 4-6 hours away -- gorgeous, and above tree line. Great hiking. People cross-country ski there, don't myself know much about that bit.

Catskills -- IANA Rock Climber but I've _heard_ there are great walls in there, and in the "Gunks". </rumor>

Kayaking -- A lot of water around here, I imagine kayaking (fresh & sea) opportunities can found. Not much white water, I'd guess, but Great Falls is renowned and DC is only four hours away.

VuongN
Take a break. Volunteer your times and do things you wouldn't have done or never had time to do before. Life is funny in that if you keep on walking, you'll end up somewhere surprising :) Good luck.
joshu
You need to take a long break. At least six months. I did this after my yahoo term was up and I needed it.
j45
What does 6 months do vs say a month?

Genuinely curious, thanks

mindviews
It gives you time for genuine discovery. Burn out, if you've ever experienced it, is not about exhaustion. It comes from forcing yourself in one direction so long that you forget all of the other things that are fulfilling to you. It takes time for all of those old desires to percolate up to the surface where you can recognize them now that you're no longer focused on that one thing. A month is great if you're balanced but exhausted and need a vacation since you're not trying to change your thinking habits. It just takes longer to recover from burn out because changing your state of mind is exactly the point.
j45
Wow, clarity.

Changing your state of mind is a beautiful way to put it.

I'm sure I've flirted or experienced some form of burnout without knowing it to be such.

I've been thinking about how you put it for the last hour.

tsantero
I just resigned from a 4 year stint in the finance industry--not exactly a startup, but the same elements of meritocracy and self-driven achievement were involved in creating the tunnel vision most here, especially the OP, might appreciate.

The result: I have been left with more "free"/me time over the past 2 months than I can remember. The first 1-2 weeks I slept in till about 11am most everyday, due to sheer exhaustion coupled with the fact that I didn't HAVE to be up and alert for anything/anybody. Since then I have been rekindling old passions and finding a new appreciation for so many things I'd forgotten in the course of my work. I can only hope in the future--when I move on to my next project/job/career---I don't take so many things for granted.

danoc
I'm guessing that one month feels like a vacation while six months is just enough time to become bored and want to get back to work.
joshu
Actually, it's at least six months.

This is not a break, it's recovering from burnout.

(I took 5 and change months off between Yahoo and Google. It wasn't enough.)

sowbug
In one month you pretty much have to do the first thing that comes to mind when the month is over.

If you take six months (or better yet a year), you have time to fall in love with an idea, go through the honeymoon stage of prototyping it over a week or two, then discovering you're not into it enough to make it a business. Repeat that cycle a few times, and eventually you'll find something with enough emotional staying power that you can't help but make it your life's work (at least until your next exit).

There's nothing saying this can't happen in a month. But if your attitude is that you're just auditioning ideas during your long time off, you're more likely to make your decision because of fit, not because of time.

By the way, if you have a significant other who doesn't appreciate seeing you idle, this approach is nice because it's indistinguishable from immediately getting back to work.

jasonkester
Six months is just about enough time off that you really start to miss working.

I'd actually recommend setting off with the goal of staying on the road for an entire year. Just travel. Nothing else. Not even a laptop along.

The cool thing about doing it this way is that you won't make it. You'll have the time of your life for 6 months or so, but then a little voice in the back of your head will start asking for more. 8 months in, your brain will just be crying out for stimulation that it can't get from figuring out which local bus to take from here to there. You'll need to work. You'll go out of your way to find a new project, to the point where you'll book a flight home so that you can get moving now.

That's what you need to recenter yourself. If you just take a month-long break, you'll never truly get off your starting point, so you won't end up where you need to be.

bh42222
I actually started something new, managed the product, a whole team, did a fair bit of design, promotion/press, successfully exited, all sorts of stuff that doesn't really fall under "Objective-C developer."

You would be perfect for a startup where that skill and experience mix is often desperately needed. But you are burned out. (Which is OK as long as you don't stay burned out.)

So do you want to teach? Join something like Y combinator but as an advisor. (Can you join without dropping most of your financial gain? Can you drop a big chunk and still have enough left to be comfortable?)

How about go into a wildly different filed, something you have a kernel of interest in but have never worked in, forest management, trapeze artists, C++ developer. (One of those suggestion was a joke.)

Or travel. (Just enjoy life for a while!)

louhong
Dan, congrats, you've accomplished quite a bit. I'll echo what others are saying and suggest taking an extended break to recharge. Visit some new places and try some new thing but most importantly, I'd also suggest reinforcing your existing relationships and to try to make some new ones. I've found that doing so increases the amount of ideas and opportunities you'll have. Figure out what your runway and burn rate is so that you're not pressured to just 'find something'. best of luck!
13rules
Love your app! Purchased it a long time ago ... thought it was well polished and easy to use. Not surprising that you got bought out!

I agree with the others that say take an extended time off. Travel, read, pursue some new hobbies, do some things you have always wanted to do, etc, etc. Let your brain relax and enjoy life ... without a doubt that time spent will lead to something great down the road. Something much better than if you dive into something new right now.

Congrats again!

fowkswe
Sublet your apartment, go to South America (Beunos Aires) while its warm. Drink coffee, eat steak and figure out your next move. More ideas will come.
solutionyogi
Dan, I am really surprised that anyone would treat you as code monkey.

I think you should get in touch with Patrick (patio11) and Thomas (tptacek) and get some tips on you how can pitch yourself better.

And yes, as a piano beginner, I love your app. :)

niels_olson
I'm learning piano along with my son. We have been using a mix of software and hardware for the last year, mainly Synthesia and a little Piano Booster. His first lesson is tonight, we're interviewing teachers for the next couple weeks. My question for you: does Etude support a midi controller via the ipad camera kit? Or is it just the sheet music, detached from any external inputs? The app page says nothing about this issue.
code_devil
If you are not hurting for money(which I doubt), I would suggest taking a nice break, travel, pursue some other skills like new language(Spanish, Portuguese), photography, cooking, volunteering, adventure sports. It will recharge you and maybe along the path you will find some interesting problems you could solve, for an instance a software solution for a problem that exists in some foreign country but you dont see the same problem in US.
rokhayakebe
1) Start advising small time entrepreneurs full time. Full time. You can join an incubator and do this, or you can simply do it alone.

2) When you are ready to do another startup you will just know it.

Edit: We spend our lifetime surviving, catching up, trying to make it. Once we make it, we realize that we never learned how to just live.

[dead] x2y
oops?
iamgilesbowkett
I'll add my voice to the "take a break" chorus. On the marketing problem -- people seeing you as a code monkey -- you could look for product development or project management jobs, and say "oh yes btw also I can code," but you're better off filing that away for future reference and travelling for a while. It's good to have a life!
andyleclair
I wish I had some advice for you, Dan, but I don't. I'm just leaving this comment to say congrats to my old roommate. You're the man now, dog!
breckinloggins
If you don't mind me saying, it sounds to me like you've come into more money and success than you've ever had and now you're feeling guilty about it. You SEE yourself as a guy who works and creates stuff, not a capitalist on a yacht; but, when you glance at your accounts, your mind is telling you that you are, in fact, a fat capitalist on a yacht telling everyone down below to row.

This is creating guilt and cognitive dissonance.

But that isn't you. The amount of zeroes on a bank statement does not a man make. The reason you went out looking for jobs even though you didn't need them is not because you were bored. It's because you wanted to convince others (yourself, really) that you haven't let success go to your head.

Well, I can tell by your post that you haven't let it go to your head. And you know what, it probably won't. Those people who get rich and then turn into complete douche-nozzles... guess what? They were douche-nozzles to begin with! Money tends to amplify one's personality, not alter it.

So relax!

Give yourself permission to:

- Buy that car or boat or whatever you've always wanted. Just keep the Tercel ;-)

- Travel, explore, learn, teach, whatever. If money is no object, the first thing I'd love to do is drive trucks for 6 months or so. The next thing would be to get my PhD. Do what you've always wanted to do if you didn't have to work... because you don't.

- Create! Use your coding skills for yourself. If you don't have the urge to write code, don't. But if you do, don't worry if it doesn't have a market or an exit strategy, just write it and feel good. Share it. You'll enjoy it again.

Bottom line: you have worked hard, developed a great product, saw it through to a nice exit, and are in a position to enjoy the fruits of your success. We at HN hereby give you permission to do so ;-)

Ixiaus
This is a great comment, OP should take this one to heart.
[dead] asciimo
"Money tends to amplify one's personality, not alter it." Brilliant, and now part of my personal world view. Thank you.
akulbe
I would say he should keep his toes wet… dabble with some small pet project, or something to keep his skills sharp. Or even learn a new tech. Just don't let your skills go dull, while you're living it up… but definitely enjoy the fruits of your labor!
jtheory
Take a break, do little projects & kick around for a bit, and contact interesting-looking companies about jobs occasionally... but don't jump for anything serious until you feel genuinely excited about it.

Give that part of your brain/spirit time to recover. As much time as it really needs, if you can afford it.

All that said, if you're interested into a side project that falls squarely into your line of experience, I have an interactive music site that needs rethinking and that's getting more & more requests on UserVoice for iPhone/iPad apps; I also have my own brainstorming on how to transform it into something really useful:

http://emusictheory.com http://eMusicTheory.uservoice.com http://brainpool.emusictheory.com

If any of these ideas strike your fancy (or if you just feel like offering advice), my contact info is in my profile.

[deleted]
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2pasc
Agree with most of the comments here - taking time off, traveling, getting inspired again by things you like might be the best. Then you could consider meeting people and seeing if you can help people out - as an advisor to get your energy and ideas back to full mode. I would love to discuss with you about your experience with the sheet music store for iPad - contact me if you can
TYPE_FASTER
What kind of jobs are you applying to? Are you applying to be a product manager then they start grilling you on code? The people want you to code is because that's what they need. Look at what your resume is conveying and only apply for positions you're really interested in. Try taking the specific technical experience off your resume and submit it to a few positions.
zyphlar
Also, as an entrepreneur you've officially graduated beyond the resume/interview/application process. The only people who fully appreciate those entrepreneurial skills are other business owners and executives; if you come in and ask me for a job coding awesome stuff, I'm mostly going to care about your code skill because someone else is handling the promotion, design, and management.

Of course you could work in a small business where having lots of diverse skills is valued, but you'll probably be vastly underpaid and overworked.

Sounds like you want to be appreciated though. Offer to work for free! If you don't need the money, help someone you identify with. Give back, pay it forward, whatever. You'll have a great time, learn a lot, and make new friends for whatever happens next.

billpatrianakos
Sounds to me like you already answered your own question. It also sounds like you might be second guessing yourself and need some reassurance. That's alright, we're only human.

If I were you, I'd take a good long break. Regroup for a third of it and relax. Then do some solo tinkering and see if anything gets you excited. Maybe you'll want to go another round with a new business at that point, maybe not.

Join another team only if you think you can handle not being the top dog. Make sure that whatever position you get, you're happy with the amount of control you have while still keeping in mind that this is someone else's baby you're caring for now. If all that's a good fit and agreeable then continue on that path. If not, do your own thing.

As for being type-cast as Engineer-Only, well, it's tricky... maybe you should leave out the part where you know how to code. You don't have to tell people you're a programmer right away. Get into the area of the business you'd like most before mentioning your other skills. Definitely mention your other skills, just not right off the bat.

Other than that I'd say congratulations, you seem like you're doing very well and have luxuries that a lot of us (me too) are striving for. It's awesome to see people like you who want to keep going round after round in entrepreneurship. Its people like you who prove that when you something out of love, not money, you truly succeed. Hopefully I helped. Good luck to you!

Aqua_Geek
> But what should a person who wants to take a break and get some broader experience [...] do?

What kind of broader experience are you looking for?

lrobb
"... nobody seems to think that I'm anything more than a code monkey"

Are you talking to the wrong people?

I realized something similar when going through tech interviews with a company (in a field I knew well) and none of the dev managers could tell me anything about their products competitive landscape... The team leads were completely unfamiliar with their competitor's features.