When Unkey was raising its seed round in 2024, we started earlier than we truly wanted to. We had a decent amount of cash in the bank but had a few driving factors for raising:
We had to start our raise early because VCs / Lawyers / everyone is less active during the holiday season.
We wanted to expand the team so we could build deploy and knew we needed cash flow to make that a reality
We had momentum
So, I set out on the adventure of raising funds for the second time. This time, we had more knowledge than our pre-seed, which was done with a lot of guesswork and a whole lot of vibes.We built a few different items to make this a reality because Unkey Deploy was just an idea and a dream we wanted to make a reality. We had:
A memo that described what we had done in the first year of Unkey, showing traction and that we could ship even with the small team we had.
A slide deck describing the future in a bit more depth
A demo showing what we believed Unkey deploy would look like, it was cobbled together with smoke and mirrors but it did work.
This was already 3x what we had for our pre-seed we did that without anything, just some production users and traction.
The raise
When we started the raise, we had a lot of interest. My calendar looked like this for a solid 3-4 weeks; the only things on my calendar were VC meetings or meetings with my co-founder.
If you have never raised a round before a couple of things:
If you've never met before and don't have an intro, expect to chat with someone who isn't a decision maker
Expect to have 2 meetings or more before you get an offer.
I went to all these meetings, pitched, emailed back and forth. Some said no, some of them we said no to. Finally, we had what we thought was the perfect deal, a little more than we wanted to raise for a seed, which meant we could hire more and go hard.
It went so wrong
We felt after some discussion that we could make this work, even though it was almost double our planned round amount.
So all I had to do was fly to SF, pitch one more time at a partner meeting, grab the term sheet, and finalize the deal. To be clear, at this point, I had done about six meetings to go over things like P/L, future, and prepping for this partner meeting. I had spent hours grinding this out with two of the team, including a senior partner.
I booked flights, hotels, and we planned where we were going to get dinner to celebrate. All three of us were flying high; my co-founder and I were discussing the plans and also secretly celebrating a great round.
Then, the Friday before my Sunday flight, I got a text that no one wants to get, whether it's from a VC, a family member, or your partner.
I wait for the call and that is where it all goes wrong.
I'm sorry we have to pull out, we can't give you the funds ... Sorry again, I really tried
Two months of work, time, and effort gone. Not to mention, have you ever tried to cancel a flight and hotel basically the night before you are supposed to fly? It's not easy.
I sat in my office, in the dark... Wondering what I did, or where it went wrong. I reached out to people, trying to get back-channel info. I heard rumors; our investors heard rumors.
I broke the news to the team. I was crushed as a CEO... I had let the team down. The new investors were still in; the follow-on investors were still in. I just didn't know how to recover... I said, "Let's pause" for a while; we need to work on a few things.
It went so right
About a month went by since the deal was dead. We had an offsite in SF, Andreas ended up being sick so ideas and thoughts which happens every single time we are in the room together had to be skipped. I met with my favorite investor Tim Chen. We talked about what went wrong and the new strategy, we worked through some stuff I needed too.
I said fuck it, I am going to spend as much time in San Francisco as I need to finalize the deal.. at the original plan 4Ms or bust. We still had money in the bank, plenty in fact. The deal needed to be done because I was annoyed for the team, upset at myself.I booked a hotel in SF in the tenderloin for 20 days... If you don't know where that is, well just ask a friend. I had a calendar booked up again, investors who were interested that I kept in the loop, new investors who had heard we were raising officially this time.I met with some great investors, I spent way too long in a hotel, ate too much terrible food. I watched that joke of a Paul vs Tyson fight.
One of those investors was Andy from Uncork, a fellow Brit. He got me, he got Unkey, he got the vision. I went to their office, we talked, I came back to their office and pitched to a couple people. They were in... Andy was so in, he ended up introducing me to a few smaller investors.I flew home, I had to attend a funeral. I am on the road and I get a text
Hey. Are you free now? In car en route to airport and can chat.
This text didn't feel like the last one, but in the back of my mind, I was thinking, "Damn... Is this a repeat?" They wanted to invest... We chatted about the deal, we chatted about the other investors.
In the end, we ended up raising $4.6 million and closed the deal on December 24th. My point of this post is: in the world of VC, shit happens; raising funds doesn't always go to plan. In the end, this deal was way better for us and the team. We raised more due to the excitement, and we had to reject some larger investments to keep the round smaller.
I want to shout out a huge amount of people, but I don't have enough time to list them all. I want to thank our investors to helped me when we were down, and the new investors who saw our vision, my partner in crime Andreas who kept the ship going while I went out. My partner who supported me through months of grinding , and all my friends, founder friends who received so many texts, discord messages at random times of the day and night.