When Is The Second Best Time To Get Help?

By Brett Fox

Handsome men working in an office“I’m sorry, but I can’t help you,” I said to Jim. “I think the best thing for you to do is sell the company. I wish you the best of luck.”

Jim’s company was past the brink of disaster and well into its death spiral. There was nothing realistic anyone could do, so I passed on advising the company.

I felt really bad for the CEO. Jim only had three months worth of cash left, and the company was losing a significant amount of money.

Jim hadn’t started looking for an investor, and finding one (unless you get really lucky) is a minimum six-month process. He needed to sell the company and fast.

That’s the worst time to ask for help, when it’s too late.

It drives me crazy, but I see this pattern repeated again and again. Entrepreneurs (and most other people too) wait until it’s way too late to get help.

Why do we do wait too long to get help?

We are told from an early age that asking for help is a sign of weakness. At least, we are in the United States.

In fact, we can be ridiculed, laughed at, or both for asking for help. We learn and we tell ourselves that asking for help is for wimps, and dammit, we’re not wimps!

So we soldier on, believing that everything will be okay.

Then we have the “Oh Shit” moment.

We’ve all been there. The moment (just like Jim had) where we realize it’s too late, and there’s nothing we can do about it.

Oh shit! Now, what do I do?

When is the Second Best Time to Get Help?

The instant we realize we need help is the second best time to get help. You can’t wait an instant or you’ll be in desperation mode. And, then it’s too late.

The problem is we delude ourselves into thinking everything is okay, that we can handle things for way too long. That’s why there is only one good time to ask for help:

Ask for help before you need the help. (And really, that's the best time to get help.)

I started my company when I was an Entrepreneur in Residence (EIR) at a venture capital firm in San Francisco. The VC firm brought me in specifically to incubate the company.

Part of the deal was one of the General Partners of the fund, Dave Epstein, became my sponsor and mentor. Dave and I hit it off. His advice was crucial to our ability to raise funding and help grow the company.

Dave was there for me before I needed the help, and I think that is so crucial for so many reasons:

  • We had already built a relationship based on trust, so…
  • When I truly needed help I knew Dave was providing advice that was in my best interest

The interesting piece to me, looking back, is that I doubt I would have hired a coach if I didn’t have the relationship with Dave. I was being cheap for no good reason.

I still almost blew it.

I don’t remember the reasons why (maybe my selective memory loss is protecting me), but I had this crazy notion that I shouldn’t pay Dave anything. All he deserved was equity.

I remember meeting with Dave at Peet’s and telling him what I wanted to do. I could see the hurt in his eyes.

He left the meeting, and wrote me an email explaining how wrong I was. Instantly, I realized that I had royally screwed up! What was I thinking?

I called Dave up, apologized, and we came to a fair agreement.

That’s why I got lucky. Dave could have easily just walked away. He was helping me, not the other way around. I am forever grateful that Dave told me I was wrong.

The money and equity Dave received were the best investment I could have made:

  • I received expert advice every step of the way, and...
  • More importantly, I had the peace of mind of having someone I trusted help guide me in my journey, and…
  • I have a lifelong business partner and friend who I will likely work with for many years to come 

My high school chemistry teacher, Mr. Kroot, had a saying: “He who asks questions remains a fool for a short time. He who does not ask questions remains a fool forever.”

It sounds almost like a fortune cookie saying. Maybe it even came out of a fortune cookie, but I liked it. The concept stuck with me.

We CEO's think we are supposed to have every answer to every question.   That simply isn’t true. And, to make things worse, we think it is a sign of weakness to ask for help.

It is not a sign of weakness to ask for help! It is a sign of strength!

There are a limited number of people you can completely confide in. You can’t completely confide in your board of directors because you’ll scare them if you do.

You can confide in a trusted lieutenant, but only too a degree, because you can scare her too. Your team expects you to have the answers, so you have to be very selective regarding who you ask for help and what you say.

That really leaves mentors and coaches, and I’m a firm believer in coaches based on my own experience.   A good mentor or coach has only your best interest in mind. Their agenda is simply to help you succeed.

Building a company is unbelievably difficult, and you’re going to need an ego to do it. Your ego, focused appropriately, can be a great tool. However, don’t let your ego get in the way.

You’re going to help, and lots of it, to win. You’re going to need great teammates.   You’re going to need good investors. You’re going to need a supportive spouse and family. And, you’re going to need a mentor or coach along the way too.

My coach and mentor was (and is) Dave. Who will yours be?

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