The Journey To Win Jason Calacanis Over

The path we took to get into the LAUNCH accelerator, starting from nothing

Mat Sherman
Call Me Mat


As of January 27th 2019, I’m happy to say that PubLoft has gotten into the LAUNCH accelerator, started and fueled by jason Calacanis and run by Jason Demant. You might call me lucky, hardworking, fortunate, etc. to be in this position, but there is only one quality that got me the right to be in this accelerator. It’s called persistence. This is a blog post that includes every interaction I had with Jason before we got into the accelerator. It’s less of a narrative and more of a look into how many times I got rejected or ignored before I got his attention enough to give us a shot.

Run it.

The first email thread/exchange

Lame. Let’s follow up to get past the autoresponder.

I had to send 4 emails to get one response from him. Only to get a flat out rejection. The most common one we get, nevertheless.

You bet your ass I put him on my non existent monthly update at the time. I created one just for him!

I’m making headway. Sure 100K GMV seems like 500 years away at the time, but we are communicating. Progress.

PubLoft died 3 days after I sent this email, in early February. My chance to get a investment from Jason was lost :(

UNTIL I brought PubLoft back again in June of that year! THAT’s another story, but a few weeks after I brought it back, I saw a tweet from Jason saying he was doing a call in #askjason episode on his podcast, This Week In Startups. I acted fast, emailed my question, and I got a call from their production lead 20 minutes later. I was on deck!

Before I knew it, I was live with Jason. Listen in at the 12:35 mark.

This was recorded on Jul 27, 2018. I finally thought I broke in. That I got his trust. So, I decided to send up a follow up email to continue keeping up the relationship.

Nothing. No response. I thought I was in the outer circle, bit still in the circle. But nope. It just meant sending more emails.

No response. So then I ask him about how he liked the blog post.

Nothing. I needed to keep trying. At the time, he was planning a conference in a few months. We applied for a pass and got one each (My cofounder..Jeremy and I). I didn’t just want to attend. I wanted to pitch.

This is the respond I got from LAUNCH’s director of marketing.

So pretty much, that didn’t help at all. Still, I had to keep penetrating. I sent Jason another monthly update.

Fun fact, this is what our growth chart looks like now in comparison.

Anyway, we got no response. I needed to keep chipping away.

AND WHAT HAPPENED NEXT?!?!? An anti climatic response. But still, it was a response.

Oh well, the action would have to happen at his event, LAUNCH Scale. Before the event, I had this email exchange with Presh.

Long story short, after waiting in line at 5:45am in the morning the second day into the conference, I got on the list to pitch Jason. I was nervous. Finally, I got to get in front of Jason Calacanis and show him what we’re working on. In front of an audience. Pressure is on. I came to the conference to pitch, and pitch I did.

Out of the three people who pitched him during that slot, he picked us as the #1 startup. After the pitch, I asked him for a second meeting. He said keep growing, said he was glad we got picked, and gave me a fistbump. I was making headway.

A few months go by and I don’t email Jason. I’m focussed on growing PubLoft. I actually wasn’t thinking about raising too much until I got another notification on my phone that Jason was taking more call in questions. I emailed in my question, and was put in the queue. I wanted to ask him about bootstrapping vs. fundraising. He gave me some great advice:

He mentioned I should apply for the accelerator multiple times, so I shot him an email asking about it.

He intro’d me via email to Demant, the accelerator director. After about a week of thinking what I wanted, I told Demant we were interested. What happened next was very fast. I get an email on the 2nd inviting me to fly up to SF for an interview on the 8th.

I go up and interview. I give my best pitch right to Jason. He’s impressed, as is the whole team. Which leads to this email:

And now we’re here. One month ago from today, I didn’t even think I was going to fundraise, yet alone join an accelerator. One month later, i’m in SF pitching VCs and growing PubLoft to be a hundred billion dollar company, with Jason’s help.

The Takeaway

I got the email on 1/9/2019. My first email to him was on 8/6/17. 1.5 years of hustling my ass off and staying persistent finally got me to a yes. Persistence is everything. Screw talent. Screw luck. If you’re persistent enough, you’ll make your own luck and people 10x more talented than you will want to be part of that luck. I 100% believe persistence is what makes founders win.

So want to be a great startup founder? Start developing your knack for persisting among everything else. You may just find that you’re creating your own luck that others want to be a part of 😋

Have a company you think Jason would like? Email me and tell me about it. Always happy to refer high potential startups to Jason and Demant for the accelerator :)