6 years of cold emails
3/7/24
About a month ago, I officially moved to NYC from SF. My previous post outlined the decision-making process for the move, but in summary, I moved because I missed/craved serendipity in my life. My time in San Francisco wasn't boring, and I didn't feel complacent, but I knew there was something more for me out there.
I moved into my apartment on January 20, 2024, with only two suitcases. I didn’t own a single piece of furniture. Since I owned no furniture and was (still am) too frugal to buy all new furniture, I became a Facebook Marketplace super-user. Little did I know the downstream impact that the time I spent on FB marketplace would have…
On FB marketplace, I found this slightly overpriced bed frame, box spring, and bedside table and messaged the seller:
Not only did I accidentally almost ghost this seller, but I showed up late… not the best first impression. Luckily, she didn’t hold a grudge and welcomed me & Quinn (my best friend) with a smile and a warm welcome to NYC. As we walked towards the furniture, we began asking each other the traditional questions:
- Where are you from?
- Where are you moving from?
- You went to X school, do you know X?
We had so much in common. She grew up in SF, I just moved from SF. She went to college in LA, I grew up in LA. Our overlap of friends and mutuals was staggering, it was almost strange we hadn’t met yet.
Ultimately, the furniture was moved, we overstayed our welcome, and it was time to go.
Quinn & I left and went to grab breakfast burritos 30 minutes later at a place recommended by her. Serendipitously, she was there, and we chitchatted, but I felt that it was too awkward to ask her out.
Then she texted me (Stevie is her friend’s puppy):
We ended up going on a date the following week. On the date I got to know her and learned that in LA, she worked at a company called Summit Series. When she said that, my eyes lit up, and immediately asked, “Summit… meaning you worked for Elliott Bisnow?”.
To 99.9% of people, that name means nothing, but to me, it meant 6 years of cold emails. Elliot Bisnow has been one of my inspirations since 2018.
At the time, I was a sophomore at Babson College working on my first company from my dorm room and was feeling unbelievably defeated. Nothing seemed to have been going right – we couldn’t raise capital, without capital, we couldn’t hire engineers, without engineers our company was simply just an idea.
I came across the book The Third Door by Alex Banyan, I forget exactly how. Growing up, I never read; the only thing I read was sparknotes to pass classes. But for the first time in my life, I read a book cover-to-cover in one sitting.
What got me hooked on the book was when Alex mentioned his mentor, Elliott Bisnow. Elliott was an eccentric individual that everyone seemed to know, respect, and attended his events whenever invited – a modern-day Gatsby, one could say. Elliott took Alex under his wing and showed him the world – literally, he took Alex to Europe. Elliott taught Alex the importance of risk, getting out of his comfort zone, and making sure people heard (truly listened) to his story.
Outwardly, Elliott introduced Alex to some of the most influential titans in the tech world (Tony Hsieh and so many more). Internally and most importantly, Elliott believed in Alex and his mission. When you’re starting a new company or pursuing any ambitious goals, people laugh at you and pray that you fail. I wanted someone to believe in me, the way that Elliott believed in Alex.
Rather than trying to meet my equivalent of Elliott, I wanted to meet Elliott. I crafted a cold email, following the same format Alex used, which he replicated from Tim Ferris, and got crickets. A few months passed and I found myself going to Utah and remembered that Elliott lived out there. I then sent him another cold email that I was going to be in town and he actually responded! He responded something along the lines of “This isn’t a sufficient reason to meet. Best of luck with your project”.
That was that, I felt discouraged but not broken. He was right. I had to ask myself why did I actually want to meet with him. What value could he provide me with, how could he help me, and why would he want to help me? I kept these learnings in the back of my mind and became more acute with intentionality when pursuing relationships with other “A-list” people later in life.
So, going back to the date, she was a bit surprised by how much I knew about Summit. She then proceeded to say that I should definitely meet Elliott, but since I was going to be in LA the following week, I should meet with her friend/mentor, who worked closely with him.
I met with her mentor, and we had a great conversation about so many things: innovation cycles, platform shifts, modern-day consumer businesses, and whether they were actually brands or just performance marketing companies in disguise. The meeting ended, we both said to stay in touch and proceeded to go our separate ways.
A few hours after the meeting, I got this text:
Three days later, I got an email with the subject line “Elliott <> Mason”
My mind: this is actually freaking happening…
I had sent numerous cold emails over the past six years to meet, and now it is happening. I knew I wouldn’t let this meeting be over Zoom, I would fly anywhere to meet him in person.
Now that I’m finally going to meet the person I have looked up to for so long, what am I even going to ask?
I wanted to know how he stayed motivated with Summit, why he wanted to buy a ski mountain, if he would do it again, the person he met that surprised him the most, his favorite investment that was unsuccessful, his favorite fund managers, what he was obsessed with these days, etc. I had many questions for him, and yet still an unanswered question on my end that I hoped he wouldn’t ask.
Why did I want to meet him…
I truthfully don’t know beyond the reason that I’m infatuated by things he had done and want to learn from him. I wasn’t looking for a job, I wasn’t looking for an investment, and I wasn’t looking for anything except his knowledge and, strangely, also his approval.
The night before we met, he sent me an email saying:
“Looking forward to meeting tomorrow. Anything you can send me that I can read ahead of time?”
I panicked. I had been thinking about starting a blog/website for the past few months, hence my move to NYC post, but never spent enough time & attention properly articulating my thoughts. I found myself in a random Mexican restaurant in Miami the day before, working on a memo for my job, had an investor meeting in a few hours, followed by a dinner. When am I going to have time to send him something? I responded by saying I was in back-to-backs and would send something over later tonight, buying myself some time.
I got back from dinner around 10 PM and started writing. I recognized that I didn’t need to write anything crazy but rather something that simply explained who I am, how I think, and what I am curious about. I put together a working framework piece (will share in another post) and sent it to him at 12:51 AM
He responded the next morning, saying that what I shared was great.
Mentally, I thought, great! He read it and thought it was compelling enough to still meet. Cool, this is a good signal.
The afternoon comes and I get to the restaurant. I stand at the front, pretending to be looking at the menu, just so I don’t look so nervous. Elliott walked in, smiled, and said hello. My nerves instantly go away.
We ordered and sat down outside. Instantly, we begin talking about Powder Mountain, how he sold it a bit ago, and his experience doing that. He then asked how my stay in Miami was treating me and why I was down there. At this time, I could do 2 things:
Say I came down here for some meetings with other VCs and prospective companies, which was true. Or..
Tell him I came down here, just to meet him.
Screw it, I choose the ladder. I told him I came down here to meet him and that I had been cold-emailing him since 2018. He chuckled and said no way, let’s find the emails. I told him my previous email address, and sure enough, he found those old emails dating back to 2018.
Our conversation continued and we began talking about his private market investment strategy, Elliott has angel invested in hundreds of companies. His strategy was to invest early and often, meaning investing at the earliest stages of companies in a high volume of deals. This strategy works when you have breakout winners, they make up for the losers and some.
Some of Elliott’s winners include Uber, Coinbase, Warby Parker, etc. Although he had/has many great winners, that didn’t come without the cost of numerous losers, too.
Although Elliott has an exceptional investing track record, that didn’t come without the cost of numerous losers and learnings, along the way. Some of his learnings were:
He indexed too much on his first impressions of people and would make decisions based on that.
Not investing in something because it didn’t resonate with him. He recognizes that just because a product/service doesn’t resonate with him, that doesn’t mean it won’t resonate with others.
Investing in various amounts based upon his level of excitement, rather than investing in consistent amounts. This makes it harder for the return profile to offset the losers.
The conversation continued to flow. We talked about why I became an investor in the first place, the style of investor I want to become, what I am obsessed with, and what companies I have conviction will become household names in the coming decade.
Elliott had to get going to pick up his child from school but told me that he was glad that we met and to Facetime him, whenever. Although our lunch ended, I knew the story was just starting – it just needed 6 years of cold emails to preempt it.
As I am currently flying back to NYC, I am shocked by what just happened. If there are things I could tell others because of this experience, it would be:
Every story has a component of luck involved.
Although luck is impossible to predict, there are ways to position yourself to increase your likelihood of being lucky.
A no today doesn’t mean it’s a no tomorrow.
There is no substitute for hard work and persistence.
You are most likely one degree of separation from your hero.
Be bold, have audacious goals, and don’t care what the naysayers think.
Adventures only happen to the adventurous. Stay curious.
-m
