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I was a $200K VC, now I’m a $0 entrepreneur – first thoughts (tryingtohackit.tumblr.com)
53 points by nycmbacoder on March 1, 2014 | hide | past | favorite | 44 comments



Leaving a $200K position where you developed a network of people who's business it is to fund companies in two of the biggest tech environments in the country is hardly starting from the bottom.


Good luck.

One alarming thing IMO in the post is the focus on getting funded vs. validating (or even selling) a product

Funding is just an ingredient (not even required always) in the recipe. The final product is the cake.

Bootstrap if you can -- build something people want (sorry for the trite startup advice) and charge for it.[1]

Don't mean to be pedantic. I just find the narrative on getting funding as a pre-req for success which has become the norm to be a bit overblown.[2]

Notes:

[1] I'm a co-founder of a bootstrapped 7-figure recurring revenue SaaS business in NYC.

[2] 2/3 of last year's tech exits were not institutionally funded -- http://www.cbinsights.com/blog/trends/global-tech-exits-repo...


He was a VC previously. VC generally has a very strange concept of entrepreneurship that seems to boil down to VC being some kind of gate keeper over who they allow to be successful by throwing money at them. It's also why most VC companies are terrible at both advice and actually making money for their investors.

The good VCs realize that they're just a minor part in helping an already successful business expand rapidly. These are the kinds of VCs who end up funding companies like WhatsApp.


A few notes regarding failures (because I think the linked quora post didn't do justice):

- Bill Gates and Paul Allen's first venture was Traf-O-Data, attempting to process traffic data. They built machines as part of this. On their "demo day", their machines didn't work. Eventually, Washington State obviated their business and they moved on to form Microsoft

- RH Macy failed seven times before founding the biggest department store in the world (I wish the number 7 was included in the response)

- Akio Morita's first product was a rice cooker, which was a self-described "memorable failure", selling less than 100 units. He then partnered with Masaru Ibuka to form Sony


Scott Adams champions "fail till you succeed" quite a bit. He's had a string of interesting failures too (listed out at the bottom): http://online.wsj.com/news/articles/SB1000142405270230462610...


There was a guy who failed 10 times...and never made it. I don't who he is because he didn't make it. Sometimes if you fail a bunch it really is time to pack it up and get a steady job.


I don't think so. You never know, he could have been successful in his 12th attempt but how could he have known if he did not try.

That's the thing about success. You know its there, you just don't know how many tries it would take you to get there.


> "being a pre-funded entrepreneur SUCKS"

You don't have to go for funding. You seem to be psyching yourself out. I don't know the details, but given your previous job, well-managed expenses should readily allow for bootstrapping.


Unless he's doing a 'get lots of users, think about money later' product. With the money he probably has set aside bootstrapping a SAAS business of something with a business model from day one would be easy and probably not require funding but otherwise he'll need funding eventually. Given his previous job and likely connections though getting some seed funding shouldn't be too hard.


I'm not sold on 'get lots of users, think about money later' products. ;)


It's interesting seeing how difficult the author finds it being an unfunded entrepreneur. Offers some perspective on how difficult it is for entrepreneurs starting off with nothing. At the very least the author probably has a decent amount of runway from working a well paid job previously. Not to mention the connections to the VC world. I'm not trying to take away from the authors struggles but trying to point out if it's that tough for them just imagine how tough it is for the rest of us.


> When I go to parties and people ask me what I’m doing

I know I'm being a little cynical here, but you should be working on your startup, not attending parties.

If you're going to sacrifice to do something, go all in.

I went through a similar process: I left a well paying engineering job to be a technical co-founder at a startup, with a 6x decrease in salary.

I had exactly $30k in savings, not including retirement, but was lucky to make an income of $24k right off the bat.

I cut my expenses to the bone--short-sold my house and moved into low-income housing, took my clothes to a seamstress to repair, bought from second hand stores, racked up credit card debt, did a couple side gigs to get a free gym membership, basically everything to conserve my cash.

It was great to get my expenses down, but it was not fun having to make tough decisions.

Ultimately, I ended up parting ways with the startup, and rejoined the workforce as a dev, but not after whittling my savings down to nothing, and racking up $10k in debt.

And

I would do it all again in a heartbeat, because it was one of the best experiences of my life (also being a part of TechStars helped).


> I know I'm being a little cynical here, but you should be working on your startup, not attending parties. If you're going to sacrifice to do something, go all in.

This is ridiculous. Devoting every waking moment to your job is a quick road to burnout and permanent failure. You need personal time to relax and blow off steam, whether that's going to parties or quietly reading in your living room.


> Devoting every waking moment to your job

I agree.

But a startup is more than a job. The mentality I had as an employee is much different than what I had as a founder.

Some start-ups are like rocket ships, and they just take off and wildly successful.

More often than not, most startups don't have that amazing trajectory right off the bat. My personal belief is that taking that extra hour to perfect a feature, or refine a pitch, or do customer outreach, or test your product, is what separates the rest of the startups--ones that make it to the next level, with those that don't.

There is some element of luck and skill involved, but it's that championship drive that is required.

Do you need time to ensure you don't crash and burn-yeah, I'm totally with that. Perhaps the poster's way to let off steam is to go to parties, which seems doubtful--though I suspect he probably doesn't really go to a lot of parties, and that it was more of a figure of speech.


Absolutely must agree with this. While you definitely need to put in a helluva lot of effort and passion and be absolutely driven... if you skip socializing, you won't just destroy your startup, you'll destroy yourself in the process. Seriously. Partying & socializing can be huge distractions for sure, but social skills atrophy, so you have got to balance the two. A startup founder that doesn't reconnect with the real world once in a while runs too much risk of building something no-one wants.


> I know I'm being a little cynical here, but you should be working on your startup, not attending parties.

to all readers: this grumpy cat judgemental attitude is not mandatory and i don't think it should be encouraged. please get a grip on reality, this world you live in filled with other people. you're allowed to go to parties and enjoy the company of other people if you are running a startup. a startup is a lot of things, but it's not a prison sentence. if it feels that way, you're doing it wrong. maybe you just suck at business.

i run a successful, profitable 7-figure revenue startup with no external funding and all of my cofounders and critical employees have always gone out to parties, both work-related and not. that doesn't mean i'm rich. that means i have a business that is expanding, which is what entrepreneurs all trying to achieve.

"partying" is not blowing 10k on a weekend in vegas or getting expensive bottle service at nightclubs, although you can certainly do that if you want to, because who am i to judge you? partying is hanging out with your coworkers at the bar, going to a birthday bbq, or celebrating someone's engagement.

i also never had to do stuff like sell my belongings and rack up credit card debt or cut my income to 1/6th of what it was. all this says to me is that you refused to get better at sales. which isn't exactly a shocker if you are on the internet extolling the virtues of shunning social interaction.


Logic fail: arguing by anecdote, ad hominem, and straw man.

The advice not to be judgmental, then in the same comment being judgmental makes you a hypocrite.

You're allowed to do whatever you want, it's your life, and your time to spend however you wish. But if you're running a company and trying to get it off the ground, I believe that every minute should be spent getting it off the ground until it is.

It means making the tough decision to miss a friend's wedding because you have an important customer demo on Monday that you have to build. It means backing on a romantic getaway with your girlfriend because an investor wants to meet you that Saturday.

Do you need down time, sure, but startups are hard work, and are going to fail, and unless you're willing to do whatever it takes to make it succeed, then what business do you have running a company.

http://blog.startupcompass.co/73-percent-of-startup-founders...

Not all founders have the benefit of keeping a good salary, a sizable savings account, or other means of maintaining their current life style.

At $24k, it didn't make sense to keep a $3k a month mortgage, so I sold my house, and was committed to extending my personal runway for as long as possible.

Living off of limited resources has nothing to do with "sucking" at sales. In our first year, we got damn close to being revenue neutral with large fortune 50 companies as customers, part of TechStars, raised a sizable seed round, and had some other very good success indicators (given that all three of us were first time founders, and this we were only 1-year old).

Since you want to "get a grip on reality"--most startups require some amount of sacrifice. That you didn't have to, is great, but certainly not the status quo.

Perhaps you've found the true path to startup success, and as such you should write a book, create a startup accelerator and make more than 7-figures in revenue.



Also, apparently every commenter on HN runs a 7-figure startup.


[deleted]


perhaps, then again, he's formerly worked at a VC firm. Getting relationship with investors shouldn't a problem.

Product Market Fit > Relationship Investors.

Of course, I don't know how many people he has on his team working on the company. If he is the face (ceo), then going to parties may help.

Still, if you build a great product, with customers who love it, you'll get funding.


> I feel VERY uncomfortable about not being the [insert respectable job title at respectable company here], and now am a pre-funded entrepreneur.

> TLDR: being a pre-funded entrepreneur SUCKS in a lot of ways, but I’m pretty sure if I ever “make it”

This guy needs to get his head out of the funding bubble. He sounds like the only goal and metric of success for his startup is to get funding. Getting funding won't make you successful; running a startup with funding that isn't growing sucks even more. In fact it will escalate the pressure and your work/life balance may get worse.


Seeing how he has (presumably) an extensive network from his VC days, and (presumably) a decent enough cash runway from having just left a well-paying career.. I would hesitate to call this "starting at the bottom".

Still.. good luck. Coming from that background it might be a bucket-of-cold-water awakening of what it actually takes to get a startup off the ground.


This is the type of post that appears on HN from time to time that reminds me of the days in the 50's and 60's when college students apparently would compete to write to Dear Abby with a story believable enough to get published. [1]

HN has absolutely nothing to go on to show that this isn't completely made up fiction and not worth the time to comment on anymore than if someone wrote "hey I wonder what it would be like if a VC left a 200k job and decided to do a startup".

Separately if this really was a former VC [2] earning 200k would seem that the publicity value of actually giving your real name would be well worth the hit on your ego.

[1] Sorry can't find a link to support because this is from memory of way back (not that way back I'm not that old..)

[2] Hey look it could be but it wouldn't surprise me at all to hear that this is complete fiction.


Despite myself, I'm impressed. I'm lucky that I'm averse to the trappings of success. For somebody who enjoys that to walk away has got to be hard. And I expect that there will be a lot of humbling experiences ahead. I look forward to hearing what happens.

One minor nit that I mention because it's a pointer to a broad problem in the industry. The writer refers to themself as "a pre-funded entrepreneur". A lot of people act as if professional investor funding is the only option. As somebody who has started businesses both with and without investor money, I strongly encourage entrepreneurs to at least keep an open mind. Be a "pre-revenue entrepreneur" or a "pre-profit entrepreneur". A culture of treating investment as a success proxy is useful for VCs, but dangerous for entrepreneurs.


I read this and had a mix of emotions.

First I kind of felt sorry for the guy, then I quickly realized there are much worse perdicaments to be in.

I was living in Louisiana as a college dropout who had sold one company and (fairly easily) making about 200k/year between one full time job and some side work.

In Louisiana that is good money, like REALLY good money, I could've easily lived for a very long time and saved a lot on that, my mortgage there is only about 1k month with all the utilities paid too.

But several months ago, I quit my job, stopped consulting and moved across the country to CA to work on my next startup.

after about 5 months I started to get very nervous, my accounts were seemingly dwindling and reveue still seemed a ways off for the startup.

So naturally we started looking for funding only coming to realize noone wants to fund a startup simply because they need the money.

Then I realized something far more important.

I have skills. I consistently made very good money before. I was capable of this again. I put a few feelers out and quickly got to help build out an awesome new product for a really great guy with deep connections.

Fast forward a few months and our little startup now has strong revenues, things are looking up on several fronts and that little consulting gig I took let me earn several thousand dollars, pay off bills and build a great relationship with someone who is sure to be a very successful first time entrepreneur (he's already had a successful career in finance).

All that to say if this guy was making 200k/year before chances are he has a good skill or set of skills and he should be looking to that to dig him out of this hole not to investors for funding for what sounds like a failing endeavor.

Most people aren't as fortunate as I was or as it sounds like this guy is. Many people in a similar situation to mine would not have had the skillset or network to pull of what I was able to and they would have likely had to get a regular job somewhere or move in with friends etc. When you have a skillset that allows you to generate large amounts of income your life just is not that hard.

Sorry for the rant, but someone should tell this guy to get over himself just a bit. Whether he believes it or not, he's a pretty lucky guy


> In Louisiana that is good money, like REALLY good money

200k is really good money everywhere.

But yeah, with the cost of living in LA, 200k/yr REALLY goes a long way.


He seems to be a victim of his own pattern recognition. This can be a paralyzing effect.


you will likely never view this time as 'the best time' you have ever had, maybe the most motivated. With all the urgency we had the whole time trying to build our company, it wasn't until the bank account was actually hitting 0 that we finally did what was necessary to get to profitability. The lesson we learned was that anything that requires time to build is not really possible as a first time entrepreneur, you need to find something that will require the least effort to get traction. I would strongly focus on getting revenues rather than getting funding.


definitely not good times IMO... the one good thing I can say about the times before being self sustaining... you don't forget, so everyday I remember just how bad it was is a huge motivating factor to keep it the way it is now - better.


> if I ever “make it”, I’ll look back on these days with fondness as the best time I ever had

Even if you fail you will look back at these days as some of the best times you ever had.


Good luck! Is this a stealth project because the service or product wasn't mentioned? If not, I would suggest to use the exposure on HN to get some feedback.


"I’m writing this because there’s a lot of widely read blogs from people who have had amazing success, but very few from people like myself, who are starting from the bottom."

$200K a year? That's the new definition of "starting from the bottom?"


I interpreted him to mean that he was making $200k a year, then recently gave it up to start his company (at which he is now making $0, thus, "the bottom").

It's certainly not "the bottom" if he has any appreciable amount of savings -- or if he's kept in the good graces of his now-former VC colleagues, whom he can call upon when the time comes to raise a round. But I don't think he meant to suggest that a $200k salary is "the bottom."


And I'm sure he made zero connections too...


Guess he lost all of it and now back to zero.


I read that as his yearly salary not savings he'd lost.


Welcome to the other side of the table!


Why no name?


About the only reason he would need to "know where all the free WiFi spots in the city are" is if he is homeless or living in a weekly motel that has no wifi. If that is the case, then he has no business trying to be an entrepreneur right now. A recent scientific study on successful people (I don't have the link handy) concluded that "success boils down to serially avoiding catastrophic failure while routinely absorbing manageable damage."

So, he has either A) fallen on extremely hard times, in which case he should go take a job, even if only for a few months while he builds up enough money for Wifi at home and at least a month-to-month apartment or B) is being overdramatic. In this case, I'm guessing it's B. That's bad, because it discourages entrepreneurship when people mistake difficulty in starting any business for poor planning or a flair for the dramatic on the part of a specific individual.


> he is homeless or living in a weekly motel that has no wifi

Yikes, you guys can be so harsh.

Some people don't like to work at home all the time.


The post implies that he must know where the wifi is and that his money is dwindling down to nothing. I have a problem with it because there are lots of people on HN thinking "maybe I can start a business" and stuff like this is needlessly discouraging. Further, if he is successful, he will have shown a wrong and very dangerous approach to starting a business. Going "all in" on something as failure prone as a new business is something no one should do unless they simply have no choice.


The only thing the author really shares is that they've quit their job, they work from cafes, and they know how much runway they have.

Nowhere do they say they plans to work from the cafe forever or the plan is to keep going until the bank account actually reaches zero. And if that is the plan, so what? The reality is there's always risk and there's no right/wrong way to start and grow a successful company.

What is important is that they're chasing something and documenting the experience from the very beginning so that others can learn from it. That's encouraging and deserves some credit.


I think he means that although he has a home and internet connection, he prefers to work from coffee shops, and for that reason, knows all the places that offer free wifi across the city.

Now, what this has to do with the article, or why he decides to work at a coffee shop, instead of a home office, I don't know.

This entire article makes no sense to me. So he left his job, and is now going to begin on a startup? That's worthy of news? No information on his startup, his plan, his goals, etc.

'I also know exactly how long my bank account will be greater than $0, unless I get funding.'

So, is he 1 week, or 1 decade from going broke? Why is he so obsessed with getting funding in the first place, and why does he say 'being a pre-funded entrepreneur SUCKS in a lot of ways'? I make a living off my recent startup, I have zero interest in funding, and enjoy my life.

Also, please stop using the term pre-funded entrepreneur. It sounds derogatory, and funding isn't a measure of success, or the end goal for everyone.


The post reads melodramatic to me too. So you were a VC? So what.

However, as a recent parent living in a small flat who enjoys collaborating, I can note that there are many reasons not to work at home, no matter how fly my wifi.




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