The Best We Ever Had

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We’ve spent a lot of time talking about ‘What Not To Dos’, meetings that left us scratching our heads, and times we’ve messed up, but that’s not to take away from all the good meetings we have had. Especially the ones that came with lessons we think about pretty much everyday.

These are the types of meetings that have helped us the most:

Meeting #1: Will you give me money?

Backstory: For 370 days, we did everything we could to get in front of one particular investor. We were told he would not meet with us, wasn’t investing, and wasn’t interested. We finally got an in and he agreed to a meeting. We were given 15 minutes.

What happened: We researched EVERYTHING we could about him, his meeting style, how he likes his coffee, when he likes the hard sell, when he doesn’t. And we brought it. At the end of the 15 minutes he said ‘let me get some skin in the game,’ and the deal was done. We left the meeting saying, all fundraising should be like this.

The Lesson: Do your homework. Always. And don’t force something to fit, when it won’t.

Meeting #2: Will you give me advice?

Backstory: We were dying to meet Alexis Maybank, one of the Gilt founders. We told her we were fundraising, trying to navigate our way, looking for mentors like her, hint hint. She just smiled.

What happened: She told us her biggest advice was when you want something, ask. Want someone to invest? Ask them. Want someone to advise? Ask.

The Lesson: Ask for what you want. Up until then, when we took meetings, we’d flirt around the issues on our mind—money, advisors, partnerships, advice. We assumed people knew why we were there and what we wanted, and were hoping they’d just bring it up. After this meeting, we realized if we wanted something, we had to be upfront.

Meeting #3: Will you tell me what to do?

Backstory: We got a chance to meet with Jon Steinberg from Buzzfeed. We had lots of questions for him on business development and management style. Read: Tell us how to do our job well.

What happened: Jon told us our only job was to fire ourselves.

The Lesson: Fire yourself everyday. A good manager hires well and hires to fix current problems they’re currently multitasking. The goal is to fire yourself from those problems and move onto the next fire and the next big thing. We are very excited to be firing ourselves.

Meeting #4: Will you work with me?

Backstory: We had a meeting with a BIG brand. Everyone told us it was a waste of our time, that 2 years would pass before anything would come from it, due to all the red tape. We went anyway.

What happened? We said we’re a startup, and we move quickly. They said if you had come to us 6 months ago, nothing would happen, but we’re ready to work with startups. In 2 weeks, we had signed and executed a partnership.

The Lesson: Work with people ready to work with you. Some brands say they want to work with startups and don’t know what that means, or don’t really mean it. You’ll waste your time to trying to make it work.

Meeting #5 Will you give me a pep talk?

Backstory: We were lucky enough to meet someone in the space who not only gave us her time and contacts, but has become an invaluable part of our extended team.

What happened: A friend introduced us to our now advisor way back when. From then on, she has understood our company’s vision and our relationship as founders in a way no one else really has been able to. On cold days in February when we are very pale and very run down, she reminds us why we are good at what we do. And she means it.

The Lesson: You need someone to support you when things are good and when they are bad who is not your mother, father, or spouse, and actually knows your business. We are lucky to have that.

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