

Ask HN: I Need Career Advice from an Experienced VC or Entrepreneur - pw0ncakes

[I would, ahem, really prefer to post this under an alternate name, but HN has a bad habit of banning new users who submit. Either that, or "You're submitting too fast" after one post is a forum bug.]<p>Obviously, I would prefer that people not try to guess at my real identity, which I'm not going to disclose in a public space such as this.<p>I'm at a startup in New York that has, in my opinion, an excellent product that is near launch, but I think we might be in trouble. One of our co-founders had what appears to be a nervous breakdown last fall and he is now unreliable and essentially non-productive. He was responsible for about 40000 lines of code and a major component of our product. The architecture of his work is poor and documentation is nonexistent. (We had known about these problems for over a year; but a year ago, we had him in the game enough to maintain his crappy code, and his productivity made him enough of a net win that we put up with him.) The code is probably "totaled" in the sense that it'd ideally be best to part ways with him, throw out his code, and rewrite these pieces again. However, I don't think we have enough runway to do so, yet I'm equally nervous about launching on buggy, bad code that none of us understand.<p>At this point, most of my time and a substantial fraction of another key developer's time is dedicated to cleaning up the messes left by this other person, whose code is a recurrent source of negative surprises (he didn't follow his stated API, which was itself a complicated POS, very well). It's stressful and a bit scary, because it leads to what at least feels like very slow progress.<p>I obviously really, really want this product and this company to succeed. Even though it might make sense, from a purely selfish perspective, to just move on to Google or Wall Street, I have no desire to do so. I've spent almost 2 years on this startup and want desperately to see it succeed, and I believe we can. I owe my best effort to my co-founders, and really believe our product has the capability to be a technological home run.<p>I'm not necessarily looking for funding-- I want the right thing to happen, and if the right thing is for us to fail and for me to move on, so be it, but I don't think this is the case. What I'm looking for advice and mentoring, preferably from someone more experienced with startups than I am, on how to turn this situation into as much of a success as is possible.<p>I'll get into more detail on this situation in private. My email is someonebornin83 at gmail dot com.<p>A few questions:<p>1. How do I determine whether we will get to launch? I absolutely cannot consider any career moves until this point, because until we've launched I have nothing to show for my time. Sadly, launching seems to recede further into the distance with each new surprise that pops up.<p>2. Apparently, it doesn't look good to VCs to have been in existence for a long time without having launched, although the nature of our product is such that we can't launch it until we get it <i>right</i>. (This isn't some throwaway CRUD app; customers will actually rely on us having our house in order from Day 1.) How do we recover from the "damage" of having operated in "stealth mode" for so long, and of once having hired (and owing back pay to) someone who actually did a lot of damage?<p>3. In the unfortunate case where we do fail, what can I do to make sure that my time in the startup isn't counted at zero at my next job? I'm 27, and I'm sick of being a nobody. My motivation for being at the startup isn't getting rich; it's that I believe in the technology/vision and also want to be a contributing player in something, rather than some entry-level cog.<p>4. I would like to be a VC entrepreneur-in-residence by 33, unless sufficiently successful outside of the VC world. (There is no doubt that I have sufficient talent. I'm +2.5-3 sigma technical and +3-3.5 sigma "big picture".) Am I on the right path? It seems like startup experience is the best kind of experience one can get for such a role, but I don't really know because I'm completely ignorant about the industry.
======
swombat
I know I'm echoing what the VCs tell you, but...

If you've been working for a year and a half and still haven't launched, that,
to me, indicates that your product will almost certainly need another year of
iteration at least before it starts making any money. Probably 50-90% of the
work that you've done so far will be scrapped when you figure out what your
customers really want. (yeah, everybody thinks they're different, but they're
not)

Combining that with "we're about to run out of runway", and this results in a
really bad picture.

I don't know what exactly is right for you - you'll have to make that
judgement call yourself - but if I were in your place, unless there is some
really significant information you're not telling us in this post, I would
revise your estimate of "I 'm at a startup in New York that has, in my
opinion, an excellent product that is near launch" - you're at a startup that
has a product that's probably 1-3 years away from being able to make
significant amounts of money, unless you have a crazy awesome sales force that
can sell ice to an eskimo.

In view of that, you should definitely take every step to plan for the likely
failure of this start-up. If you've built a product that needs to be perfect
from day one, you've built a product that's probably going to fail (and if
that's an inherent requirement of the product category, then it's not a good
product category for a start-up).

So, looking at your specific questions:

1) Assume it won't launch at all. What can you salvage? Well, actually, you do
have a lot to show for it. If you worked at a large corp and built a product
for them that they never launched, you wouldn't have "nothing to show for it".
You must have learned a lot on the way. I know (from personal experience) it's
hard to be positive when your startup is falling apart, but it's really a
matter of perspective. Discuss this with a positive, can-do friend who'll help
you bring out the positives if you ever need to interview.

2) See earlier comments. You can't recover from that damage - you need to
launch and iterate. If you can't launch and iterate, you're dead in the water.

3) That's all a matter of how you sell yourself. I would suggest looking for
other start-ups to join though. They definitely won't look down on your
experience as "worthless". Some corporate departments might - but those are
probably not the ones you want to work at anyway. Others are desperate to hire
"entrepreneurial people". If you sell your experience right you should be able
to make it worth your while.

4) That's not really related to the rest of the post. Forget about that for
now and focus on the cataclysm unfolding around you. You'll need all your wits
on the present moment.

PS: Feel free to come hang around in #startups on freenode for further
discussion of this.

------
arghnoname
I'm not going to address your specific questions (I lack the proper
experience), but I'll question an assumption.

I once worked on a project where the main developer was fired after 3 _years_
of failing to get the product out the door. There was a lot of code, and it
was colossally bad. Worse than anything I had ever seen on The Daily WTF. I
and another developer that were put on this project to take it over begged and
pleaded that it just had to be rewritten.

We were denied. They didn't know how bad it was, surely. We tried going over
heards. We made presentations. We e-mailed around particularly egregious
examples, but this was a codebase where the total awful was greater than the
sum of the individual horrors, so to speak.

Anyway, over three years this guy, bad as he was, must have worked hard. There
was lots of it and we were just expected to 'fix it' since it was 'almost
done.' Nevermind that nothing worked. Slowly, steadily, whenever we'd go to
fix a bug we would (in stealth) rewrite whatever section we were in.
Eventually we started writing adapters to help the new cleaned up code
communicate with the bad, bizarre, inconceivable horrors or API design that
the old code had. Eventually, like replacing the handle of an axe on one
occasion and the head on another, we had a whole new code base that we had
come to be proud of.

The lesson I took away from this is it's sort of limitless what this kind of
refactoring can accomplish, even if it's not the most enjoyable way to go
about fixing a mess. With something like your situation, it's how I'd
recommend going about fixing it, since these sorts of things are hard to
understand in the aggregate anyway.

Most bugs in any piece of software are concentrated in relatively small
proportions of the code. Start there and you might be able to launch with much
of his code intact, with the most damaging removed or repaired, and fix the
rest in transit.

Or not. You know your situation better than I possibly could, but it's
something to think about.

~~~
exit
what kind of software product was this? web based / desktop application / etc
?

~~~
arghnoname
It had a back-end that communicated with a web based front-end. It was
something that would be sold to companies that had the specific need the
product addressed and the web component was essentially the GUI. Some clients
would communicate directly with the back-end with their own or with modified
interfaces. You could tickle the backend as a web service.

------
brk
<2cents>

1) There is no way to "determine" this directly. Launch is when YOU (you being
the company) say it is.

2) Not necessarily IME, but expect a management shakeup if funding does occur.
Your current leadership may be considered unfundable, but if the product is
viable the company (legal entity) may be fundable, albeit with some chaos.

3) You can't, however if you've learned things and can articulate how you have
learned and grown from the experience (on paper and in person) you should be
fine.

4) This is an unlikely outcome on your current path. You would need to have
shown some exceptional leadership and insight skills to get to an EIR role. It
is _possible_ to do that in the next 6 years, but you would need a launch in
the next 12 months, then 3-4 years of steep growth, with yourself playing a
highly active role in managing a large aspect of the business through that
growth curve. IE: you need to deeply experience the growth and success of a
company, be involved in the details, and have clear responsibility for key
decisions. You would _likely_ be best off seeing this through and then
founding/co-founding something on your own (and taking that corp to an equity
event that is considered a success).

</2cents>

~~~
pw0ncakes
Thanks.

1\. There are certain milestones we have to meet before we can launch. We have
a great product, but we have some holes we have to fill. I can't get more
specific here.

2\. The leadership of the company is excellent. We're in trouble (in _my_
estimation only) because no startup can afford to have a key person take a
dive, and every developer is key.

3\. Thanks.

4\. Why is it this way? My understanding, and I could be mistaken, of the EIR
role is that it's someone who works at startups while sponsored and mentored
by the VC firm. I would be excellent in such a position, not now (and possibly
never) as an EIR-to-CEO, but as an EIR-to-senior developer (if such a thing
exists).

------
9oliYQjP
You haven't truly started a business until you've made your first sale. Sure,
this is an opinion, but it's one that I firmly believe in. From what I know of
people who "start businesses" these days, most end up not actually making any
money. It's a huge resource sink until they fail. Life isn't a Disney movie,
but failure isn't the end of the world either.

One thing you haven't mentioned at all is whether you think you will launch
and have a revenue stream. How are you going to make money? Do you have
customers lined up or just some hopes and prayers that people will flock to
your product/service once launched? The reason I ask is that I also firmly
believe (again an opinion) that when you do launch, you probably have another
2 or 3 years before you'll get your head above water financially.

I started a business when I was younger and failed (quit gracefully but the
trajectory was never headed up). I was hired by somebody I did business with;
and trust me when I tell you that on paper I am the prototype of mediocrity.
It was actually my mom who suggested that "maybe I stick it out in a real
company so I gain some experience". It was a comment that at the time was
piercing and hurtful but ultimately right. I did really well at that job,
realized I was better at some things than I expected, and that I was worse at
some things than I thought I was. I treated it as a learning experience, and
the money didn't hurt either.

A lot of companies would be happy to hire you. In their minds, you may not
have made it as an entrepreneur, but you'd make a great intrapreneur: someone
who is entrepreneurial minded and can succeed within the confines of a safe
sandbox which is the company.

~~~
jonpaul
Well said. I completely agree with you first point. If you haven't made any
money, you have a hobby not a business.

~~~
9oliYQjP
I'd like to elaborate on what I said, because some people make take it as me
being dismissive of startup attempts. That wasn't my intention. But if you
have launched a startup and never actually had a customer, then you've missed
the quintessential characteristic of entrepreneurship. Lots of employees
develop great ideas into prototypes within the confines of a company. If
that's what you like to do, you don't need to be an entrepreneur to get paid
to do it.

But starting a business means actually having to _sell_ something. It's one
thing to develop a product or service. It's an entirely different thing to
sell it. Once your product/service is on the market, you have to deal with a
whole bunch of problems that the first group of people who merely start a
"business" but don't actually sell anything, will never have to encounter.

First and foremost, you actually will have customers. Customers are needy.
Some are jerks. Some are wonderful and will send you cookies because you've
brought a little sunshine to their life. But all customers have expectations
and those expectations need to be serviced. Developing an idea into something
tangible is in part a measure of somebody's ability to anticipate market
needs. Dealing with customers is about how well you can react and fill in the
things you did not anticipate or didn't get entirely correct.

Additionally, you'll have competitors. While your customers are pulling you in
all sorts of directions with their own needs and wants, your competitors will
be sizing you up in their sniper scopes. Having competitors is probably only
one of a handful of things in modern life that resembles being prey. You know
how fidgety squirrels are and how they are constantly scouring for food only
to store it away for future use? Having competition is _kind_ of like that.
You will have to balance being a squirrel that is too safe and consequently
gets mired down in fear with being one who is so haphazard that she gets mowed
down by a car she forgot to look out for while running across the street.

If you have ever started a startup but never actually sold anything, you will
never have encountered any customers. You might have encountered some
competition that was so overwhelming that you never made it out of the womb,
so-to-speak. And in that case, life is just unfair but you'll never know how
well you would have stood up given equal footing. Regardless, having
experience with customers and competitors are to me, the fundamentals of
business. I think a lot of startups are great at developing things, but things
are not products or services until they're actually sold.

If you like to develop things and are doing so at the moment, that does not
make you a startup or a business. It means you like to develop things.
Employees can do that. Employees can get paid very good money to do that. As
an employee, you can even form your own little team and manage people like you
would in a startup or a business. You can launch products and services as an
employee too. But until you've found a way to _sell_ that thing you've
developed, I personally don't think you've started your business. A hotdog
vendor down the street is way ahead of you in that respect.

------
starkfist
4\. You aren't "+3.5 sigma big picture" if you went 2 years without launching
anything, you let a dude waste your time for 2 years, you can't determine
whether you will launch, you think you have a product that can't launch until
you "get it right" and your dream in life is to be an EIR (but you are
"completely ignorant about the industry")...

~~~
medianama
come on.. don't rub it in

~~~
hga
He's not "rubbing it in", he's pointing out some harsh truths. Perhaps mostly
about how most people define "big picture", but in general they need to be
said.

I'll go one step further; in a followup, the author said "[T]he leadership of
the company is excellent" when that is demonstrably not so. Just sticking to
the technical management part of things, the leadership of this company has
known, and should have realized what it meant, that for that last year they
had a key coder who was producing unmaintainable code. For the last half year
this guy has been melting down and is now non-functional. Yet he is still a
"co-founder".

They don't seem to have then necessary sense of urgency about this emergency
("We're in trouble (in _my_ estimation only) because no startup can afford to
have a key person take a dive, and every developer is key.").

This is an existential crisis for the venture and there's probably nothing
more important for them to do at the moment than resolving it with a good
plan, which I just don't get the impression is happening.

~~~
pw0ncakes
Fair point.

We believed that the unmaintainable code problem would be less of an issue
after launch, and that this person knew his codebase well enough to keep it on
life support until that point, at which we could hire people to fix the
problem, possibly with aid of post-launch funding. We assumed it was benign
"technical debt" -- a bad technical situation that can be paid off later when
resources are less scarce.

What we didn't count on was the meltdown of the person responsible for the
problematic code. In hindsight, we should have seen it coming, but it seems
like there are always things going wrong in a startup, and _everything_ seems
urgent.

I've wanted for a while to fire this guy, throw out his code, and rebuild
everything from scratch, but have been under the impression that we don't have
the time/turning room to do this. I'm not experienced enough to know the
externals (e.g. how hard it is to get funding, etc.) and whether or not this
is the case.

~~~
pclark
why do you want to be an EIR?

~~~
pw0ncakes
I like programming and solving problems, but I also like working at the big
picture and being aware of the financial aspect. I'd be a great VC, although
I'm also a pretty strong programmer. It'd be nice to straddle both worlds and
learn from the best on each side.

------
jacquesm
If you want to stand a chance at '4' I'd suggest you take charge. Now.

Not next month, every day spent in the current setup is a day wasted in the
longer term, you need to change direction towards some form of launch, even if
it is with an incomplete but minimally viable product.

The 'one more feature' or 'one more milestone before launch' mentality is the
most certain way to get killed. If you can't launch before you've completed
those milestones _and_ you have internal troubles your chanes of survival
depend on the depth of your pockets, and the speed with which you can get the
situation resolved.

Your company seems to have two founder problems, not just one, both a
developer-founder _and_ the CEO are not currently functioning as they should.

If you are the CEO call a meeting of your co-founders, outline your issues,
put up a plan of action and ask for a vote of confidence, if you are not the
CEO then try to get your CEO on board. If he won't acknowledge the gravity of
the situation you have a real problem.

What I really don't understand is how you've managed to hold out this long
without any source of income or funding, 2 years is a long long time.

I wish you much good luck and wisdom, you will need it by the looks of it.

------
jtrautman
I see several actions you can take to salvage your work on this startup:

> Address the personnel conflict. This conflict may be resolved working with a
> neutral party in a facilitated meeting or a mediation. Bring all co-founders
> together and deal with the anger and frustration that’s been accumulating,
> decide upon a fair settlement with the co-founder that addresses his
> performance and the quality of his work (whether he stays or goes), then
> work together to plot out an action plan, assign responsibility for the
> unfinished code, and agree how to get to the finish line. Several other
> commenters have given opinions about how to salvage the work and get the
> code out the door.

> Recruit some pilot customers. Finding some early adopters will give you
> invaluable insight about your market. Creating a product that fits the
> market’s needs is more important than making something perfect before it
> gets a debut. In my experience at other software companies, products
> significantly improved once we had a small core of users that let us know
> what their priorities were. We thought we understood the market, but found
> that it was very challenging to gain insight about rapidly evolving business
> needs without working directly with customers. You don’t need many, but find
> two or three companies that will be enthusiastic pilots.

> Reframe your thinking about the experience you’ve gained. If you do not
> resolve the conflict and must abandon the business venture, you can work
> with a neutral person to debrief what you learned over the past two years. I
> have worked for many different businesses over the course of my career. The
> size and success of the company was not a deciding factor in my professional
> development, my work was. However, when I had strong feelings about my
> experience at a company it was often difficult for me to be objective and
> capture the points where I developed and grew professionally. Find a neutral
> coach who can draw the positives out of this experience. It will be a
> springboard to help you see your current situation in a positive light and
> that will energize you.

Taking these steps will help you get resolution about the company so you can
move on, either as a viable business or as a recruitable talent in the startup
community.

------
jonpaul
I say this out of sincerity, and not to be a jerk. You want to be a
"somebody"? Then launch. Two years without a launch is very concerning. Start
a blog and work on it DAILY. Force others to recognize you in your industry as
an expert.

I realize that I'm saying this from an outsider's perspective and I don't know
the insider's scoop. Part of being a successful startup requires discovering
your MVP (minimum viable product) early. This will then allow you validate
your business model and focus on customer development. I highly encourage you
to research Steve Blank (if you haven't) and his Customer Development model.
Read "Customer Development" [<http://en.wikipedia.org/wiki/Steven_Gary_Blank>]

I wish you the best of luck and good success.

------
jfischer
It sounds like the leadership at your startup needs to make the hard decision
to fire the co-founder outright or to reducing him to a very limited
consulting role (no coding, just answering questions about his code).

I think that you would have a great story to tell to future interviewers if
you can get the bad code under control and launch the product (even if the
startup fails). I would have more confidence in someone who overcame adversity
than someone who never faced any problems.

The "+2.5-3 sigma technical and +3-3.5 sigma big picture" stuff would be a big
turn-off to me. There's a lot of really smart and talented people in this
industry.

~~~
pw0ncakes
_I think that you would have a great story to tell to future interviewers if
you can get the bad code under control and launch the product_

Great point. Thanks.

 _The "+2.5-3 sigma technical and +3-3.5 sigma big picture" stuff would be a
big turn-off to me. There's a lot of really smart and talented people in this
industry._

Sorry, I guess that does sound arrogant. To be fair, there are a lot of +3, +4
sigma minds in technology. Most of the programmers I've worked with I would
put in the "+3 sigma technical" category (because I've worked with some
awesome people at great companies). My "sigma" estimates were relative to the
white-collar world in general. My point is that I have more than enough to
make a great VC, EIR, et al with sufficient mentoring, not that I'm any kind
of stand-out (relative to the HN-sphere, I'm definitely not, as there are a
lot of people smarter than I am here).

~~~
gregschlom
Hehe, I suppose that if I have to ask, it's probably not a good sign about my
own "sigma", but what's this +3 sigma stuff anyways?

From what I understand, it must be some way to asses someone's intelligence,
like the IQ, but I've never heard of it.

Come to think about the IQ, it follows a normal distribution, and sigma is how
we note standard deviation. Is this the kind of sigma you are talking about?

~~~
arghnoname
I don't know what it is either, but guessed along the lines you are guessing.
Of course, a Z-value of 3.09 would put you in the 99.9 percentile, so that
seems far fetched.

~~~
chegra
I think you are correct with your assumptions. But I think he needs to explain
himself in this department. I didn't think it added any value to his post
since it is unsupported. Maybe he could have quoted his GPA, or IQ[still
dubious]. I think most people don't put their trust in numbers either way,
they go for what did you accomplished[especially VC, they want to know the
numbers behind your financial efforts]. I was quite surprised at how hard some
of the other posters judged his "big picture" evaluation. I think maybe he has
a problem with acting not thinking. I think he knows what to do, but just
simply not doing it.

------
faramarz
To even be considered for an EIR role at a venture fund, you need to have
previously exited successfully or failed miserably.

If you don't launch, you're risking everything.

If you do launch, albeit it not 100% ready, at the very LEAST you have a case
study on your hands that will help you in other venture and employments. At
the very MOST, the people (consumers and investors) see the value proposition
in your product and decide to give you a try.

Don't burn the assets, launch with what you got and do whatever it takes to
land prototype in front of the right people.

Also, you need to address the co-founder problem right now before it get's
more complicated.

------
MaysonL
Find a customer to whom you can explain the total situation, and offer them a
deal: in return for them supporting you now, you will give them cheap service
for the duration, and the best customer service in the world. Not the most
likely outcome, but if your product is as potentially good as you say, there
may be someone out there willing to gamble on it.

------
jfornear
I can only relate to having worked hard on something and not having anything
to show for it.

I just try and salvage as much as I can and try to fit it into a story that
communicates my overall goals.

------
themullet
Would think about on 1 - does the product work? has it been tested, could you
get it infront of clients?

As for the 40k lines of his code and his component; write up tests, refactor
it where need be and if the worse comes to the worse launch with buggy code
and update after it's out there and you know if it's worth fixing!

------
shareme
I am going to say something that you my have trouble reading or hearing..

You waited too long to handle the cofounder developer problem. Cut your losses
now and get your second wind and attack the other startup ideas in your mind

~~~
pw0ncakes
I agree wholeheartedly on "waited too long". We all tried to keep him
motivated and productive, but weren't able to in the end.

Honestly, the current venture, minus the bad apple and the rickety code he has
written, is still (in my estimation) better than any other ideas in my mind.
We still have excellent people and a great idea.

