It’s not every day you get to ask Ron Miller about his predictions for the tech landscape. Ron is the former enterprise reporter at TechCrunch and current operating partner and editorial director at boldstart ventures, where he writes and produces the FastForward blog and newsletter. I had the opportunity to connect with Ron about how he thinks 2026 will play out, the leap of faith he took by joining the new media, the joy he got from publishing his first article on FastForward, and so much more.
The full transcript of the conversation can be found below, but if you only have time for a quick scan, check out our “Dialed-in Snapshot” for the points you can’t miss!
Dialed-In Snapchat
- From journalist to founder: Ron took a leap of faith to build FastForward, an entire publication from scratch. He paralleled pitching his new venture for the first time with the trials of being a startup founder – an interesting coincidence, given his years at TechCrunch.
- Mindset shift toward new media: In new media, Ron believes trust should be placed in the individual and their work. Initial skepticism from PR teams shifted to active engagement only once his first few profiles were published.
- Ron’s “AI Adventures” and reality check: Ron talked about his love-hate relationship with AI. Later, he divulged his prediction for 2026 that the AI bubble is primed to burst. Expectations for the technology have been blown out of proportion, and we’re in for a cold “AI November.”
- The “right” conference is a content goldmine: Ron emphasized the importance of content available on-site for him to consume and the invaluable “organic flow” that comes with being in person that virtual attendance cannot replicate.
- AI talk is becoming stale: Ron is eager to learn about other technologies in executives’ orbits that aren’t being talked about yet. He also plans to cover more of the startup journey in 2026.
You started FastForward in the first week of December last year. What’s one thing you learned about yourself during that process?
When I started, I had already been a journalist for a long time. I worked for existing platforms. And, for both me and the boldstart partners, that (FastForward) was a leap of faith on both sides.
They knew me through TechCrunch. I met Ed Sim and Elliot Durbin, who were and are the two principals for boldstart, about eight years ago. At the time, I was writing a report on the New York City startup scene, and we established a connection then because they’re deep in enterprise technology. I covered them a lot because they funded cutting-edge enterprise startups (and still do), and I used them as sources.
When we discussed working together, they knew I could write an article and submit it to a platform with a staff of reporters at my side. But, they didn’t know if I could take something and build it. And frankly, I wasn’t sure either. I had built other things, but an entire publication, no. Getting FastForward off the ground was a challenge for me, from the design process of the logo to building the site and working with an outside firm.
I remember the logo. There were numerous minor iterations, but I liked that it stated “powered by boldstart”. I wanted the rest of the site to reflect that.
While that was happening, I was writing the first supply of content.
You’ve written for multiple platforms over the years. Can you compare the feeling of the first article you ever wrote to publishing your first on FastForward?
It was tremendously gratifying. We started with an idea. The whole thing was by the seat of our pants; you never know if it will truly work. And leaving TechCrunch, I had to pitch myself for the first time, especially for that first supply of content.
You mentioned in your anniversary post that the script was flipped with PR. What does your inbox look like today?
It was hard for me to read all the emails I received when I was at TechCrunch. I spent my mornings processing and asking, “Does this look interesting?”
Then, when I left TechCrunch, even though I had 10 years of experience and all that came with it, that didn’t seem to matter to those same people. I contacted PR teams, saying, "I have a new project, would you like to be part of it?” and they would respond that they want to see how it looks first. They were cautious. It felt very much like what a startup founder would face, convincing people that what they were doing was worth it.
I think you’d agree that a mindset shift is necessary with new media: people are trusting you and your work, not the outlet.
That's right. I hoped that would be the case, but it wasn’t always. My theory was, once we got the first four profiles up on the site – Salesforce, Blackstone, Juniper, and PayPal – others would say, “Oh, this is cool. I want my executive on there.” And it worked. That week, when I launched, PR teams from prominent companies were in my inbox. I was confident, but I didn’t know what was going to happen. The second hurdle was publishing and seeing what happened with readership. There was also the newsletter that evolved throughout the year.
The newsletter continues to evolve. I published a newsletter before at FierceMarkets. I looked at more than a dozen newsletters from others for inspiration. I began with the original version, looking at industry trends. Over the last six weeks, I’ve reacted to news. I’m also using the newsletter to drive clicks back to the blog. I’ll never have the audience I had at TechCrunch again. I have a small fraction of that, but the audience is committed. And I think that’s the future of media. It’s small publications with small staffs, with committed audiences who cover niche topics.
Anyone you follow or admire?
Look at what Alex Konrad is doing at Upstarts Media, covering startups, or what Casey Newton is doing at Platformer. He covers those big AI platforms, and it’s just him. It’s amazing what he puts together every week. I’m so impressed with him.
Talk to me about your “AI Adventures.”
That was something I was doing on LinkedIn. In that section of the newsletter, I write about my experiences with AI. I want my readers to follow along with my AI discovery journey. Some of the things I use AI for are amazing. It helps with my research and speeds up my process as an individual publishing a publication solo every week, but there are still warts to AI.
Can you talk about experiments you’ve tried with the newsletter or blog? Compared to working at TechCrunch, the autonomy to try something and know the results, whether it worked or not, must be a big change.
I learned about blogging in 2003 at a blogging conference in Boston. The speaker was Rafat Ali, who had just started paidContent.org. He sold that to The Guardian. Then, in 2012, he started a travel website called Skift. So this was a person who knew a lot about publishing, but back then, he was just a guy. He obviously later became very successful.
I was attracted to blogging because of the independence it gave me as a writer. You didn’t have to beg at the door of the people who own the printing press or website anymore. After that conference, I literally went home and started a blog. I had it for 15 to 20 years. I only recently (in the last few years) shut it down. The ability to publish myself was an amazing feeling. It brings back memories.
With FastForward, there’s pressure on me to produce all this content every week. I’m in a good rhythm now, but there’s a lot of work that goes into doing something yourself. There’s gratification, also, but there’s pressure to keep producing.
How is that different from working at TechCrunch?
One of the things I liked about working at TechCrunch was independence. When the management changed, some of that independence started to be pulled back.
How is the relationship with boldstart?
They’re involved very little. They let me do my thing. We have meetings on occasion.
We recently had our one-year. We talked through potential tweaks we could make to the blog. One of the opportunities discussed was not just focusing on enterprise trends, but also trends impacting startups. To be clear, not about the portfolio because that always seemed counterproductive for us. We always wanted to be seen as above the fray, rather than directly promoting portfolio companies.
That startup trend writing is similar to the work I did with TechCrunch+. I’ve ventured there the past few weeks, since we had the conversation, to try it out.
How do you treat conferences? What is the bar to get you to travel?
It’s part of what I do for sure. I have to go out and make these relationships. Going to conferences has several benefits for me.
One is that I stay on top of trends, which I need to do to remain interesting. Two, I meet people, some of whom I could profile. Others can be sources for me to contact for comments.
I recently attended a one-day event because I was on the West Coast. That turned out to be incredible. I was there for six hours and ended up writing three pieces, so it was very useful. Sometimes you go for content, but usually it’s the act of networking that’s most helpful for me as a journalist.
How I pick and choose what I’ll go to: the content matters. I’ll look at the agenda and see who’s coming and what they’re talking about. That’s one thing. It has to be worthwhile and in my wheelhouse. There’s also the factor of the distance I have to travel. If it’s a one-day conference in San Francisco, I’m on the East Coast, so I’m probably not going to that, no matter how good it is.
One thing that gets forgotten is that your time is everything. You don’t have a team to fall back on. It’s all you.
You don't have anybody to cover for you. Yeah, exactly. That's another thing I take into consideration when I'm traveling. It puts more pressure on me to produce my content.
Sometimes I can write on an airplane, sometimes I can't. It depends. Sometimes the person in front of you reclines, and then you can’t even open your laptop. I go in with the best of intentions. Or if the WiFi is wonky, then I can't really work because I don’t have access to my transcript or collateral materials. There’s definitely that aspect of it.
I didn't attend Dreamforce, but I still wrote about it. I watched the stream online and was pre-briefed on the news beforehand. Did I necessarily have to be there? No.
The difference being there, on the ground, is that you get the perspective. For Dreamforce, to get my perspective on Salesforce, I asked some sources for comments. But it’s not the same as having those conversations in the hall with fellow journalists, analysts, and others in the middle of it.
We learned during the pandemic that being together as humans is better than not.
I’ll be at re:Invent again this year. When I attend a conference like that, I like to do several things. I might not even sit in the auditorium during the keynotes because it’s just so crazy. I might sit in my hotel room and watch the stream. Then, I’ll go and talk to people and set up interviews, hopefully with individuals from AWS. Then, if I meet anyone at their events and parties, I enjoy chatting with them. It’s like a huge organic flow that happens in a flywheel because you’re on the ground and not virtual.
Speaking to CIOs and CTOs every week, what’s a constant that comes up in every interview?
Obviously, AI. We talk about AI an egregious amount. I’d prefer to change things up a little in upcoming interviews. I want to ask: What’s one thing that you’re thinking about that’s not AI? Every interview is starting to feel a little too similar, even though they’re all different and organic. You want to touch AI. AI is touching everything. So for me, it’s become let’s have an AI section of the conversation. I just don't want the interviews to be that predictable, though.
So I'm thinking about how I can change up the interviews? Although AI is front and center in everybody's mind. You can't get away from it. It's always, “How is it going to work?” “Are you finding that you're getting a return on investment?” “How do you look at it?” “How do you talk to customers about it?”
The interesting thing about AI is that it’s very different from, say, Kubernetes or cloud computing. The difference is the CEO isn't going to come to you as the CIO or the CTO and say, “I just read about Kubernetes. My kid is using it.”
Don’t get me wrong, we should be using AI. But with AI, everyone has an unreasonable set of expectations because it’s so accessible. And it wasn’t always that way. It used to be niche machine learning models and natural language processing. Now, all of a sudden, with generative AI, we’re all interacting with it either through voice or typing.
There's a lot of pressure on the technology side of the house to make something happen because there's so much FOMO from leadership.
One of the reasons I do my “Adventures in AI” series is to show people that the reality of using these tools does not always match the hype. Not the executives I speak with, but too many others believe they can cut headcount because they have this technology. And I think that that's the unrealistic expectations that those folks have to deal with.
We’re coming up on the end of the year, prediction time for many Highwire clients. I thought it would be fun to ask you if you'd like to make a prediction for next year. Will we still be talking about agentic AI 12 months from now? Will the AI bubble burst as many are predicting?
The AI bubble is going to burst. The amount of money being thrown around and poured into this, the amount of data center capacity they’re building, all under the belief that it will make AI smarter. I don’t think that’s necessarily going to play out that way.
It’s not like software. When you upgrade software, you get more functionality. With AI, some barriers are tough to overcome when you hit them. I think we saw that with ChatGPT-4 and 5. We expected a huge leap, and we didn’t get it.
ChatGPT was a breakthrough, that’s undeniable. I remember in April 2023, I would go to conferences, and people would say, “Wow. If ChatGPT-4 is like this, I couldn’t imagine what 5, 6, and 7 are going to be like.” And, it doesn’t work that way. I don’t claim to be an AI expert. I’m a journalist. I talk to my people. I’m not technically savvy in that way. The individuals I trust say it doesn’t move in a straight line. There are detours where you hit a barrier, and it’s difficult to overcome that barrier. There’s this belief that brute force is the answer, but that won’t get us past those bumps.
We’re going to conclude not too far into the New Year that maybe we need to put the brakes on. I don’t think it’ll be like an AI Winter, where it will be a decade before we return to AI. I think it's going to be an AI November, where the masses will hunker down and rethink their strategies because right now, the hype doesn’t match the reality.
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