“I’d like to be Chief Operating Officer,” Randy (not his real name) said to me.

We had already agreed on Randy’s ownership in the company and his salary, so all that was left was the title. Randy had over 30 years experience, and he was a true heavyweight.

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“I think that makes sense,” I said.

Giving Randy the COO title was one of the worst mistakes I made as CEO.

Why? We didn’t need a Chief Operating Officer. And we likely wouldn’t need a COO for a long, long time.

I had violated the basic rule for titles: Give someone the title they deserve, not what they want.

Randy wanted to be COO for all the wrong reasons. Randy had never been a C-level executive before, so becoming COO fed his ego. …


“What you did was incredible,” the associate at the venture capital firm, “Donald Ventures,” said to me. “I’ve never seen anyone handle ‘Raul’ like that.”

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We were walking out of a diligence meeting at DV’s office on Sand Hill Road. This meeting was the last meeting we would have with Raul’s fund before they gave us a term sheet.

Raul was a legendary tough guy. He was only 5′ 4″, but he was intimidating. His words were biting, and he didn’t like hearing bullshit.

The questions Raul wanted to ask were around my background and the background of one of my co-founders, “Randy.” …


My wife and I were going through old videos the other day, and we stumbled upon this video of Avery’s fourth birthday party. I invited Nancy and her son Ethan to the party. Nancy used to work for me a couple years before that.

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The video consists of me talking excitedly to Nancy about starting my company. At the time I was an EIR (Entrepreneur in Residence) for a VC fund in San Francisco, and the video is painful for me to watch.

I’m telling Nancy, in this very authoritative way, about how things would play out over the next year. Everything I said to Nancy was pretty much wrong. …


“You should give us the authority to spend up to $1,000,” “Randy,” one of my co-founders, said to me, at a staff meeting, right after we received our initial funding. Then, he continued, “And we should each have a company credit card.”

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Randy’s requests sound reasonable, don’t they? How much damage can someone do with $1,000 of spending authority? And, you can always rescind someone’s credit card, right?

I looked at Randy, and, as calmly as I could, I said, “No. That’s not something I’m willing to do.”

“Why not!” Randy exploded.

“Cash is the one thing we have control over,” I said. “And, for now, I want to keep a tight control on cash.” …


“Hi Brett, it’s Carlos. Uh…”

“What’s the issue, Carlos?” I asked our HR VP.

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“You know the salary you wanted to pay your new engineer, Fred? “Bob” (the CEO) wants to reduce it by $20,000.”

“You’ve gotta be kidding,” I said. “I thought the offer was approved.”

“What can I tell you,” Carlos said. “Bob changed his mind.”

“Unbelievable,” I said laughing sarcastically. “I’ll try and sell it, but don’t hold your breath.”

I paused and said, “This is how you screw up a company.” Then I slammed the phone down in disgust.

You can’t expect to hire A players if you pay them C player salaries.

I hung up the phone with Carlos, and I mentally prepared myself to speak with Fred again. I knew it was a fools errand, but I didn’t have a choice. …


“I’m managing three companies,” “Jason” said to me. It was our first conversation, and warning lights started going off.

“Tell me about the three companies?” I said.

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Jason said, “The first company is a software company which is doing about $5 million in revenue. The second company is a SaaS company doing about $1 million in revenue. And the third company is my law practice.”

“Interesting,” I responded. “How many direct reports do you have across the three companies?”

Jason said, “Let me think about that.” Then after a very long pause, he said, “17.”

“Wow. That’s a lot,” I said. …


“I think we’re getting really close to getting funding,” I said to myself. We had just had another VC pass, but THE WAY VCs were passing seemed different to me.

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Maybe we were getting close to getting funded. More likely we weren’t.

But you’re so strung out from hearing “no” all the time that you grasp onto anything you can to give you and your team hope.

Was I lying or deluding myself?

Maybe.

I was finally right. But it took two years and 63 VCs turning us down to get there.

So maybe I wasn’t lying so much as I was rationalizing or exaggerating. …


There are some things you never forget when you’re a startup CEO, and watching my co-founder and VP Sales, “Ken,” run around the office yelling, “Hey, Hey!” after we got our first order, is one of them.

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We had just soft launched our first product, the TS1001. We didn’t do any marketing. Nothing at all. All we did was put our first product on our very crappy, Go Daddy, website.

And within 24 hours, someone magically bought our first product.

The reason we did a soft launch was we wanted to test our systems before the big launch, where would announce 16 products at once, a couple months later. …


“Congratulations,” I said to “Ray,” a CEO I have been working with. “Getting funding in three weeks is quite an accomplishment.”

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“Thank you,” Ray responded.

“Especially, after what you’d been through in your first two rounds of funding, you deserve a little bit of a different tune.”

Then I paused and said, “But don’t let up until the money is in the bank.”

“I’m not,” Ray reassured me. “It’s my sole focus.”

You have leverage when your company looks like it’s going to be a unicorn.

What’s interesting, in Ray’s case, is that he is closing the company’s biggest round of funding yet, $50 million. …


“Tell me about your background,” I said to “John.” “Jim,” my co-founder who recommended John to me as our VP Engineering, and I were having lunch with John at Bucks.

Bucks, for those of you not living in Silicon Valley, is an institution. It’s located in Woodside right near Sand Hill Road. Everyone loves Bucks.

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I am the exception because I hate Bucks. The food is mediocre at best, and it’s way too loud.

Nevertheless, there we were. Having lunch at Bucks.

John started going through his bio with me. It was very impressive. I already knew that he had worked at Maxim like I had. I was off running a different area of the company at the time, so I never worked with John, but Jim had. …

About

brett fox

I work with startup CEOs to help them grow their businesses . I built several businesses from $0 to >$100M. Learn more at www.brettjfox.com

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