Bloody noses and panic attacks — go find a mentor.

I’m writing this to let founders know that it’s OK — preferred — that you ask for help.

Before I was a venture capitalist, I was founder and CEO of a software company called Leverage Software. We were really early into enterprise social networking — I mean really early — 2001 early. I owned the domain name “”. I paid $2,100 for it. In 2003 I met with someone at JP Morgan and he told me it was foolish to use the term social networking — that no one would take me serious. I owe him an email :). I digress.

In 2007 my lead investor told me he wanted to put me out of business, just moments after offering to invest $8m into the company. The reason was all about ego. Just after offering $8m, he said he wanted to lead the company as CEO, for which I was both flattered and confused — it’s a long story but he was a bad — really bad — investor. I left that meeting knowing 2 things:

1. I had to sell my butt off because he wouldn’t let us raise money

2. It was up to my team and me to do it

What I learned very quickly was that my cofounder wasn’t on my side — he was influenced by the investor, he was concerned about losing his job — he was afraid. It was a shit-show. We rolled into 2008 which was a horrific time to sell software as everyone was cutting budgets. It was also a terrible time to raise money (we may see something like that in 2016). Even when we received a decent term sheet from investors, my bad investor — let’s call him Mr. Major — would decline it (I signed a bad term sheet and he had to approve everything). Fortunately, I had a great sales team who helped us through and we were cash flow positive for about 3 years, but it was brutal.

What few people knew is that I was making payroll every 2 weeks by selling invoices. It became a best practice within the company — close a deal, sell the paper, get funded, receive the AR, exchange the paper for cash — on every single deal we did — more than 100 deals a year. It was/is completely ethical but not the best way to live from day to day.

That bloody noses were commonplace — so bad that I visited the emergency room once as I couldn’t stop it for 20 to 30 minutes and it was a constant stream of blood. On that one occasion I was sitting in South Park so people in the office wouldn’t see me, and a guy having lunch said “dude — you need to go to the hospital — you’re gonna bleed to death”, so I did. It actually stopped in the emergency room, but I must have lost a couple pints of blood.

That I thought I was having a heart-attach on 2 or more occasions was not good. All of this was likely, though not diagnosed, caused by the huge amount of stress I endured. The doctors thought the bloody noses were simply weak capillaries and the panic-attack like symptoms were lack of food after intense exercise. I doubt it. After I sold the company these symptoms all went away, and I haven’t had them a single time since. That’s just too huge a coincidence for me. That stress, which I thought I was handling well, was the result of “owning” everything. I had no one to ask for help, or thought I didn’t. I would discuss with friends but they couldn’t help other than to be an empathetic ear. Venting, though, probably did keep me sane. I needed something more though, someone to help me solve the problem or offer sound advice specific to the business — to help me through it or to tell me to quit. I think that was part of the problem — there was no way I was giving up — no way I would quit, even after assuming personal liability to debtors, paying salaries with credit cards, and foregoing salary. This also pre-dates the fail-fast and failure is OK mantra.

Even with hindsight, I’m not sure who I would have asked. What I did learn is that I should have had a mentor, and you should too. If I run into this situation now — which I haven’t and don’t expect to, there are a dozen people I can go to vent or to ask for great advice.

I suppose the purpose of my story is to encourage you to find someone who can help. Don’t carry the burden yourself. I’m seeing founders fall into deep depression — and I don’t want that to happen to you. Until you find someone else, reach out to me if this is happening to you. It’s important to have someone there for you — an investor, mentor, friend — someone who can make an impact. Find that person before you need them — now if possible — in case you do need them later. Entrepreneurship is funny — I’ve seen some who I think give up too soon, without asking me for help, but it’s likely in the best interest of their health. I do believe, however, that they could survive another day if they had a support group to rely on. Go find yours today.