#7: AI Consulting with Darby and Mike Gioia (Pickaxe AI Co-Founder)

Full video transcript

Are you a consultant? Are you interested in partnering with AI companies? Recently I had the opportunity to join Mike Gioia, one of the co-founders of Pickaxe, a tool that we use and a sponsor of our Gen AI University Scale with AI Summit Series, to break down how I’ve approached partnering with AI companies over the years — starting from Jasper back in early 2021 to a number of different examples since. This interview is basically a share of how I’ve approached developing strategic partnerships with different AI companies and brands, and cultivating a community to create an ecosystem that allows these partnerships to live on and add value to those subscribed to our community and our YouTube channel. If you’re into AI and consulting, I think you’ll get a lot out of this interview — at the very least, some ideas for creating more strategic partnerships with AI companies in your industry. All right, let’s dive in.

Mike: So here we are — all of you probably know me, or maybe you don’t, maybe I’m just an email in your inbox. I’m Mike, one of the co-founders of Pickaxe. We’ve done several webinars with a lot of content about how to use Pickaxe, how to do X, how to do Y. We’re starting to do more content around what a lot of users are doing, which is starting profitable AI businesses and AI consultancies — a pretty new idea that didn’t really exist before. Part of that is selling AI products like Pickaxe or building client products, but part of it is just being part of the whole AI ecosystem. It’s a huge opportunity: could someone who didn’t know how to code get a job as a “vibe coder”? People who understand this technology, and especially understand the human element of how to provide value with AI tools, have a big opportunity. We’ve been running a webinar series — one on how to sell AI to larger organizations, and this one on how to partner with AI companies, because a lot of you aren’t just making tools, you’re putting on events, building ecosystems, all sorts of things. So we brought in Darby Rollins to talk about this. He was literally the first user of Jasper AI, before ChatGPT even existed. He’s been in the AI game a while, has tons of clients, runs Gen AI University, puts on large summits, and knows how to connect people and organizations in the AI community to create valuable partnerships. I’ll turn it over to him — questions go in the chat, and we’ll open up to broader Q&A at the end.

Darby: Thank you so much, Mike, and thanks to everyone tuning in — I see a lot of familiar faces and a lot of new ones. I’ll start with a little background. I’m Darby Rollins, an entrepreneur, and I founded Gen AI University in 2021, shortly after becoming Jasper AI’s first paying user at the very end of December 2020. At the time I was running an e-commerce consultancy specializing in strategic creative direction for Amazon listings, and I was pretty burnt out. I had the opportunity to check out a tool then called Conversion AI, then Jarvis — Disney made them change the name after Jasper for using the word “Jarvis” — and that’s history now. I got the opportunity because I was living with Jasper’s CMO at the time, Austin Distel, one of my best friends, who actually officiated my wedding this past year. That was the starting point for Jasper, which over the next eighteen months raised a $150 million Series A at a $1.5 billion valuation — one of the fastest-growing startups in Y Combinator history.

The momentum from starting Jasper stemmed from me being frustrated trying to stand apart in a world where everyone claimed they could build AI listings. I locked myself in my room for a weekend and used Jasper to help me write a book — a 110-page short book about Amazon copywriting. I shared it with the community and it struck a chord: other consultants and business owners, especially those who’d never written a book, wanted to know how to use AI to write one too. That kicked off a 7-Day Book Challenge, which compounded into monthly trainings and workshops over the next eighteen months. Jasper raised its round about a month before ChatGPT came out, and everything exploded in terms of AI awareness. Through this time I built a community that has been fostering an ecosystem — through virtual and now in-person events — that brings together AI products, brands, and other entrepreneurs and consultants to grow their businesses with AI.

Thinking about how to partner with AI companies, I can point to a few specific situations. At the end of the day, these partnerships all happened as a result of direct one-on-one relationships with a founder, marketing officer, or executive at the company, or from someone looking to bring people into their organization. One early example, before ChatGPT hit the scene, was working with Jasper to develop templates — the kind of thing you could now build any number of with a tool like Pickaxe. I was then introduced to John Benson, a legend in direct-response copywriting, who at the time had a company called Copy Pro (now Benson, bnsn.ai). We were trying to figure out how to integrate his product with AI systems, and Jasper was on the cutting edge of that. The idea for the partnership stemmed from a community member who asked, “Jasper is great, but what if we could create a full sales letter with it in the style of John Benson?” I reached out to someone I knew through a mastermind who had worked with Benson before, and over about six months we developed an integration with his “mini VSL” template and framework inside Jasper. Right around then ChatGPT came out, and we started figuring out how to combine it with Jasper to help Copy Pro’s clients write better copy.

In that case I was effectively acting as a deal broker — I saw one company with an audience looking for ways to use Jasper more effectively, and another company whose customers wanted to write better copy, and if I could get the two to talk, it was a win for everyone. Both partnerships started from a direct relationship with someone at the company and understanding the problems their customer base was experiencing, then finding or creating content or tools to solve that problem.

That partnership led to John being one of the speakers at our very first Scale with AI Summit, back around 2022, right before ChatGPT came out. This ties into a second theme beyond one-on-one relationships: hosting events has been incredibly valuable, opening up more relationships and partnerships, and building our YouTube channel around tutorials and demonstrations. From that first Summit I had the opportunity to collaborate with UC Berkeley’s Changemaker program, developing a course for their spring semester with one of my partners, Kelly Tenny — an opportunity that came directly from putting on a virtual event and showing people how to actually use these tools. Looking back, one project tends to compound into the next, and the deeper the relationships I build with partners and AI tools that already have good products and a customer base, the easier the conversation becomes. If you say, “I have an audience that loves your product and wants to see more of it, and you want to reach more people like my audience — what can we do?” that’s not a hard conversation to open.

The Scale with AI Summit is now an ongoing event and podcast series from our YouTube channel, and it gives us the capacity to support sponsors with private workshops. Gamma, a popular AI presentation and website-building tool with a very large user base, has been our Platinum sponsor for both the 2024 and 2025 Summit Series. They’re open to working with creators, foster a large creator community, listen to their users, and are investing heavily in growth — I saw a figure of something like 40 million active users, which blows my mind. When you’re already using a tool in your business, that’s a great opportunity to think about how to add value for them without them needing to do anything, starting to build the relationship in advance. People join our Summit and our community because they trust the type of content we bring and the people we support — and Mike, you’re a great example of this too with Pickaxe, because I used your tool, other people in our community used your tool, and when I asked my mastermind for potential sponsors before the last Summit, one of our members knew you and made an introduction.

That shows that even if you don’t know someone directly at a company, you might know someone who does. You’re not here to spam-blast ten thousand AI companies — I’d rather be direct with strategic partners because it’s the start of a long-term relationship where co-creation leads to other opportunities. It takes time and effort to put these relationships together; there’s no easy button. It’s about knowing who you want to work with, identifying a genuinely good product (not hype that’s going to fall away), actually using it, and then using AI itself to help find ways to add value — researching companies, identifying initiatives you could make introductions for, or leveraging an audience or ecosystem you’re already nurturing. If you have those channels and distribution set up, it makes it that much easier for a potential partner to say yes to an initial conversation.

Playing the long game matters — it would have been a failure if I ran the last Summit, got the sponsors we did, and then none of them wanted to come back. My number-one focus was delivering an exceptional event that put sponsors in a great light and brought a lot of value to our community. We succeeded, and all of our sponsors re-upped for the next Summit. That’s how I measure success with these relationships.

On the flip side, even companies not in a position to pay for event sponsorship often have referral or affiliate programs. I use Descript so much that I became an affiliate, and I’m creating content around how we produce and distribute content on our YouTube channels throughout the Summit — if that turns into an official sponsorship down the line, great, but even just driving sales and subscribers their way opens the door to a bigger conversation. All of this comes back to building the community from the beginning — it’s always been our foundation — while putting the spotlight on other people and building the ecosystem, because there are so many smart people doing incredible things with AI. Even when a major deal isn’t imminent, having some ongoing way to maintain the relationship keeps you top of mind. I saw so many people become “AI experts” almost overnight during the ChatGPT boom, and most of them aren’t around anymore, as opposed to those sticking around and building their audience over the long haul. That’s why I’ve focused on community and partnerships that partners will keep investing in as we help educate their audience and keep them top of mind for our community — the more I can help my partners win, the more our community wins too.

I don’t tend to work with massive enterprise-level companies — there’s a lot of money in those contracts, but for any consultant getting into this, the starting question is: who do you want to serve, and what problem are you solving for them? That’s no different than before AI existed; we just have more advanced tools now to solve those problems faster. Don’t forget that human-to-human connection is what people crave most right now, especially as everyone tries to automate themselves out of the business. I lean into being more human, connecting with customers face to face — that’s not for everybody, but if you’re not clear on the problem you’re solving and who you’re solving it for, you’ll have a hard time making these partnerships work. If you can communicate non-technically for the average business owner how a tool works for them, an AI company — usually full of brilliant, technical people who just want to keep building — will happily talk to you if you can be their salesperson.

Mike: I can give the company perspective quickly. It’ll be hard to partner with a company like OpenAI because they’re inundated, but for smaller companies — from Pickaxe’s perspective, we really want to engage with the community and put on webinars, but we’re not in a position to hire a full-time community manager. A lot of these startups have people wearing many hats, so whenever someone reaches out offering to do part of that work for us for free, more or less, in exchange for some value, we’re pretty much always open to it. It’s been a great growth strategy for Pickaxe and a lot of AI companies — the more you work those relationships, the bigger both of you get, and the higher level you can play at.

Darby: Reading through the comments — Ron asked whether there’s a specific metric to look for in a potential partner, like referrals, presentations with their app, or total community members. My answer: they probably need an established user base, and if they already have a legitimate affiliate program that pays people out and is easy to get in touch with, that’s one indicator — especially platforms like PartnerStack, which I believe Gamma uses. Depending on their stage, they may have an affiliate manager, or titles like partnership manager or strategic partner director as they expand. It can be a good idea to ask a tool like Perplexity for a list of relevant titles to look for. Community-wise, Gamma stood out immediately because they were actively engaging with their creator community — they had a Slack channel with multiple threads sharing bugs and feature updates, very transparent.

Mike: Another thing — at a company as small as Pickaxe, we read every email, so you’ll probably reach the founders just by using the info email. Just keep it simple; a fifteen-paragraph proposal is hard to work through. Make it an easy yes: “Hey, I’m doing this, would love you to join.” I also help program an AI film conference in LA every year, and we try to make sponsor asks just as simple. The first year we gave a lot of freebies to build the relationship, on the idea that this company is small today but will be bigger next year, so you want to take the long view and pick companies and people you like, even if they can’t pay much yet.

Darby: One of the tools we’ve developed for that is a free book called Buyer’s Brief — available on Amazon, but free if you join our community — which has been my lead-in for opening conversations with companies integrating AI. Before Pickaxe, we built a system called MarketSauce, a market-research method using AI prompts and frameworks to help entrepreneurs get inside the mind of their market. I use these reports to lead with value in advance. For example, Shel, a small business consultant, and I built a partnership where we sold versions of these reports as an add-on to her client services, and now she’s become a go-to for delivering that kind of AI-powered service. That’s one way to use AI to open a partnership conversation as a consultant — using a framework you’ve already developed, which tools like Pickaxe can now help build almost instantly.

Another approach, which I know Robert and others do effectively, is reactivation campaigns — reviving dead lists a SaaS or AI company might be sitting on. If a company has been spending heavily on marketing but isn’t doing effective lead follow-up, that’s a prime opportunity to reactivate some of those leads. An easy way to make it a yes is proposing you don’t get paid until money actually hits their account from a reactivation, tracked through an affiliate link if they have one. These are relatively simple campaigns to set up, and if a company is getting a hundred or a thousand new users a month, there’s likely an opportunity falling through the cracks in leads they’ve already paid for. AI now lets you analyze lists and write copy, emails, and follow-up sequences in a fraction of the time it used to take.

Mike: When you reached out, Darby, you already had a big reputation and a well-developed ecosystem, so it was a no-brainer for us. But there are lesser versions of that too — next week we’re doing a webinar on building lead-generation tools with a guy named Drew Donaldson. He’s not at Darby’s level, but he reached out with a solid idea for the webinar and some other ideas, so we were happy to do it.

Travis (via chat): In your experience, what content format has been most effective in driving engagement for AI partnerships — YouTube videos, webinars, challenges, online courses, summits, live events?

Darby: My answer is whichever format you’re in the best position to execute well. If you can do a live event, great, but if your audience is spread across a hundred countries, that’s probably not the move. All of those formats can be interesting to an AI company if done reasonably well.

Mike: We’ve had success with all of them — YouTube, webinars, five-day challenges, courses, summits, live events. It’s varied by what was working at a given time and what came next.

Darby: That was a big learning from our initial 7-Day Book Challenges — we led with those, but running them on a regular cadence became a burnout event for me as the host. Still, they were incredibly effective for engagement because they gave people a clear goal and timeline, and they led to so many partnerships and community members — we still have people in our community from 2022 who joined through those early challenges. Webinars are great depending on the audience and what’s offered on the back end. We’ve also run courses that completely fell flat — an eight-week program drove a bit more upfront revenue, but the actual engagement wasn’t congruent with where we wanted to keep putting our time, so we’ve shifted toward more micro-content and condensed the length of Summit sessions.