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Regular readers will know that I’m so inspired by Kirsten Green’s unconventional, self-made journey to become a venture capitalist that I did a lengthy profile of her for our last PandoQuarterly. A few weeks ago at dinner, I asked her to reflect on the one person who she couldn’t have done it without.

She barely hesitated before naming Sandy Colen of Apex Capital.

The story is one of my favorites in our “My Big Break” series so far, because it’s a lesson of why you should always stay in touch with smart people you connect with. So often people starting their careers look around trying to find “A MENTOR!” expecting that person will just burst into our lives fully formed and ready to do anything to help us. But a real mentor is earned. Most great mentorships take years of lunches, dinners, coffees, and conversations. In the case of Green, it took more than a decade. But boy did it pay off.

[Note: The My Big Break series is being sponsored by Braintree's Ignition program, so you'll only see their ads around "My Big Break" pieces. But the series was conceived, commissioned and edited entirely by Pando. Braintree had no input whatsoever in the editorial. For more on our policy towards single sponsor series like this one, see here.]

Here’s the story of a multi-year relationship suddenly leading to a $5 million check in her own words:

“My first investor in Forerunner [was my big break], without a doubt.

I met Sandy in 1997. He was just starting his business, and he had a job posting for an analyst. I interviewed for the analyst job, and I thought he was great, and I think he thought I was great.

I heard through the recruiter he wanted to offer me a job, and I thought ‘Hmmm… it’s two guys with– I don’t know– $20 million bucks starting a hedge fund. I’m 24. I want to go work at Montgomery Securities. There are a lot of people there, and I want to learn from other people.’

So I ended up being a retail analyst, and Sandy used to be a retail analyst before he started his fund. Even though his fund invested in all categories, he still had a particular interest in retail, so that enabled us to further our relationship and talk more.

From there we stayed in touch. Sometimes we’d talk more often than not. Sometimes it’d be a year, and we wouldn’t talk. He’d kind of always check back in with me and say ‘Do you want to work here?’ and every time I had some other idea about what I was doing. We got to a place, maybe after we’d known each other for ten years, where we would have lunch three times a year, and it’d always be a four hour lunch.

Sandy came to one of those lunches one day, and he’d been tracking what I was doing. [This was before Green had started Forerunner and was doing one-off retail investments.] He was pretty into what I was working on, so he made me a pretty ridiculous job offer, or at least wanted to start talking about one. He was looking for succession planning, and we’d always talked about working together. Meanwhile he’d built a $2 billion fund and had been extraordinarily successful. He was like, ‘If it was about the money, you should have come here.’

I said, ‘I’m flattered and it’s so tempting but I am right here about to seize the moment of what I’ve always wanted to do. I want to invest in the next generation of companies; new, early stage retail companies, where there are exciting new ideas.’

By this time, I’d met the team from Birchbox, and I’d met the team from Warby Parker, so I had two tangible examples. He probably saw my energy and enthusiasm, and he said ‘You want to mess around with these small companies?’ He probably tried every which way to talk me out of it. And I said ‘I do. I just want to do it.’

‘Alright, how much money do you need?’ he asked.

And I was like, ‘What?…um…$5 million.’ .

‘Alright,’ he said, ‘if that’s what it’s going to take to get in business with you, we’ll do it.’

And I got in the car, and I called my husband: ‘OH MY GOD!’

He’s been the best partner ever. He’s a super smart guy and a shrewd business person, so after lunch there were reams of work to do to support that, but he said it in a moment in a conversation and he followed through on it.”

What do you think he saw in you?

“I wanted to do nothing other than that. I don’t care what sexy job he put in front of me, this was what I wanted to do. And I hadn’t decided yesterday, I’d been working on it for years. I’d been slugging it out, and I think he had that moment of ‘There’s nothing else this person is going to do. If we’re ever going to work together that’s what we’re gonna have to do.’

And Sandy was probably the only person I knew well enough that I was comfortable enough to ask for that first check then.”

Photography by Amy Harrity for Pando.

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