One year at boldstart

A year ago this week, I started my journey at boldstart. I had spent the previous decade at TechCrunch covering enterprise technology, but over time I had begun to grow restless. As I started to look outwardly for a new challenge, I landed on boldstart, but it was not by mere happenstance.

I first met boldstart’s principals Ed Sim and Eliot Durbin in 2018 on a trip to New York with my colleague Danny Crichton (who now runs editorial at Lux Capital). Danny had the idea to do an in-depth look at the enterprise startup scene in the city. While mostly known for consumer tech at the time, Manhattan also had a lesser-known but thriving enterprise infrastructure startup scene – and we dug into it.

That was the start of my relationship with boldstart, whose portfolio companies tended to align with my coverage areas, and over time my path would cross with Ed and Eliot more than a few times. When I started thinking about a new job, I reached out to them, and a series of conversations ensued that would eventually result in them hiring me as Operating Partner-Editorial Director last summer.

When I began thinking about what I wanted to do next, I asked some industry friends for advice and one key recommendation was: build something. In other words, my next move shouldn’t be lateral, but one where I could make my mark.

I started talking to Ed, Eliot and Ellen Chisa last April and we discussed the role, responsibilities and how to make it work. Over time, we eventually conceived of a blog and a newsletter that would become FastForward.

For starters, we envisioned me profiling CIOs and CISOs at large companies. That eventually broadened to include CTOs, VPs of engineering, Heads of AI — essentially, anyone who helped set technology policy at a company.

But at the start it was just talk. They had no way of knowing if I could execute on that vision. We both took a leap of faith.

Digging in

The first several months were all about building, and I felt very much like the startup founders I had covered for the previous decade at TechCrunch. I had a vision, one I had to articulate to other people, but what I lacked was a product — in this case, a publication.

At TechCrunch, I was the gatekeeper. PR came to me asking for access, and I had to decide who to cover, but in this role, at least for starters, the script was flipped. I had to approach large-company PR reps for access, and their job was to make sure I was legit.

Yes, I had decades of experience covering enterprise tech behind me, including my time at TechCrunch, but without something to show them, I sometimes ran into resistance. Our initial plan was to build the site and newsletter in parallel with writing the first four or five profiles, but it wasn’t always easy getting folks to agree to talk to me. Between my contacts and the partners, however, we eventually landed some big wins, and it felt like what I imagine landing your first sales must be like, more than a hint of exhilaration. 

Our first batch included executives from Salesforce, Blackstone, Juniper and PayPal. The hope was that once we had a proof of concept with some well-known organizations, the script would flip back and people would ask to be profiled. We had no way of knowing if that would work, but it was our hypothesis.

Delivering the goods

We launched the first week of December last year while I was at AWS re:Invent. There is no perfect time to launch. There’s always a reason not to go, including being in Las Vegas attending a major conference. But with the blog and newsletter design process done, my training on how to use them complete and a package of stories written, it was go time.

The blog went live on December 3, 2024. My first newsletter followed that Friday. And as people read it, the theory turned into reality. I began getting inquiries to be involved instead of having to ask. Now when I approach companies, I have a portfolio of 36 profiles and growing to show people. I have a website chock full of content. I have an archive of 36 newsletters under my belt.

Over time, I’ve gone from trying to figure out how this was going to work, which while exciting was also rather stressful, to building a rhythm and routine to my work week. I start off with the profile, then write an in-depth article/analysis about something in the week’s news and finally the commentary and the rest of the newsletter contents. Along the way, I also conduct interviews with the profile subjects and industry experts.

One year later, looking back, we were able to execute on the ideas we discussed in our meetings prior to me being hired. In year two, we will look to build on that vision, make the most of our growing network and continue moving forward. 

It may be the first anniversary, but I feel like we are still just getting started. Thanks to everyone who subscribes to the newsletter and reads the blog. And a big thanks to the executives and industry experts who have helped bring the content to life. 

The first year went by in a blink. I can't wait to see what year two brings.

Featured photo by Kelly Common on Unsplash