By T.A. McCann — May 6, 2026

Four tech waves. Six companies. Here’s what I’m building next.

I’ve been lucky. Lucky to be building during four major technology shifts: the internet, SaaS/web services, mobile/social, and now AI, and to have learned something useful from each one. Not by being the smartest person in the room, but by being around others building at the same time. By being early, staying close to the work, and paying attention to what was changing before most people had a name for it.

After eight years helping other founders build at Pioneer Square Labs, I’ve decided it’s time to get back on the water myself. I’m refocusing my time as CEO of Lev, my sixth company as a founder, while staying connected to PSL as a Venture Partner. This is the longer version of why.

How it started

I built my first website in 1995. Most people didn’t have email yet. I ran a small web consulting shop called Soft Labour, helping businesses figure out what the internet meant for them, which mostly meant explaining why they needed a website at all. Then I co-founded HelpShare, one of the earliest attempts at web-based Q&A. Think Quora, a decade before Quora: connect people who have questions with people who have answers. The idea came from a belief I’ve carried ever since, that knowledge is more valuable when it’s shared, and it’s shaped almost everything I’ve done since.

What that era taught me, beyond the obvious lessons about burn rate and business models, was that major technology shifts don’t just change industries. They change who gets to build. The internet created an entirely new class of founder: people who had never worked in enterprise software, never raised institutional capital, never run an engineering team. Suddenly, they were starting companies. I’ve watched that pattern repeat with every shift since.

HelpShare didn’t make it. The dot-com bubble burst, taking a lot of good ideas down with it, and ours was one of them. That failure, and the need for a job, paycheck, and recovery, landed me at Microsoft, one of the better unplanned course corrections of my career.

Microsoft, and the threads that never left me

At Microsoft, I got my first real education in what enterprise software actually looks like at scale, how to build and structure engineering teams, how to ship reliably to large organizations, and what quality and security mean when thousands of companies are depending on your infrastructure every day. It was foundational in ways I didn’t fully appreciate until I was building again without that safety net.

I ran the Hosted Exchange business, one of the first serious attempts to deliver enterprise email as a cloud service, and a direct precursor to what became Office 365. With Exchange 2003, we also built consistent desktop, web, and mobile experiences for the same product, giving users the same interface and data regardless of how or where they worked. At the time,to take on the hosted Exchange work, to pursue the spam strategy, and to have that was genuinely novel. The device/experience convergence everyone takes for granted now was something we were actively figuring out then.

The other thread was machine learning. I worked on early ML systems for fighting spam, collecting and sharing metadata on spam signals across the entire Exchange network, one of the first practical, large-scale deployments of machine learning in a real product. That was over twenty years ago. When people talk about AI as something new, I have to smile. The foundations were laid a long time ago. What’s changed is the scale, the accessibility, and the speed.

Microsoft was a great environment. I was genuinely encouraged to be entrepreneurial, to take on the hosted Exchange work, to pursue the spam strategy, and to have real ownership over hard problems. But it wasn’t the same as being a founder. I’d had that before, and I wanted it back. That’s what led me to Polaris (thx Steve Arnold) and then on to Vulcan.

Following the Microsoft chapter, I ended up at Vulcan Labs, Paul Allen’s studio. Working alongside Steve Hall, who ran Vulcan Capital, we built a system to generate and validate new ideas, then spin out the ones worth betting on. It was my first real exposure to the studio model: approaching company creation as a process rather than a lottery.

One of those ideas became Gist. It was also shaped by my time on Exchange. I’d spent years thinking about contacts, calendars, messages, and how they relate to each other. Your professional network lives across a dozen fragmented systems, and there’s no single place that brings it together intelligently. Gist was a social address book that fixed that. Early relationship intelligence. BlackBerry acquired it in 2011.

Gist was also where I met Brad Feld. He was an early investor and became a board member, collaborator, and one of the most important mentors of my career. I’ve written about his influence on how I think, the give-first ethos that shapes how I operate. Foundry Group, Brad’s firm, is also one of PSL’s anchor investors, which is part of why I joined PSL years later. He’s now watching the same AI trends I am, and building toward them too. That tells me something.

After Gist, I co-founded Rival IQ and had a hand in Senosis. Rival IQ tackled a real problem in the social era: every brand had a presence across a dozen platforms and no visibility into what competitors were doing or what content was actually working. Competitive intelligence for the social era. We sold to NetBase in 2021. Senosis used the sensors already in your phone to deliver clinical-grade health diagnostics, no new hardware, just smarter software on the device everyone carried. Google acquired it. Learning by doing and seeing where the market is going.

Give first and a mentoring mindset

Running alongside all of this has been a thread I’ve never fully separated from the building work: mentoring.

Since HelpShare, with the belief that knowledge is more valuable when it’s shared, I’ve tried to practice what Techstars calls “give first”. Hundreds of founders through Techstars, Startup Weekend, CDL, UW, PSL, and a lot of conversations in between. The same questions come up constantly: how to find the right problem, how to validate early assumptions, how to find customers, how to think about the team, and how to know when to pivot. Smart people who deserved more than “let’s get coffee.”

What I kept noticing was that the answers weren’t that different from one founder to the next. The hard phases are the same. The questions are similar. The failures often happen for the same reasons. If that knowledge is systematic and shareable, why does every founder have to rediscover it from scratch?

PSL and the process

In April 2018, I joined Pioneer Square Labs as Managing Director. Greg Gottesman and the PSL partners had built something rare: a studio model that actually worked at scale, backed by patient investors who understood what systematic company creation requires. Greg’s belief in the model and in me shaped much of what followed. Brad’s involvement as an investor and advisor was also part of why I said yes.

Eight years at PSL gave me things I couldn’t have gotten anywhere else. I learned to see companies from both sides of the table. I got sharper at spotting what separates the founding teams that figure it out from the ones that don’t. I got to work alongside some of the best operators I’ve ever known.

And I became, if I’m honest, the process guy. I was always pushing to make the studio model more rigorous, more repeatable, more teachable. Over several years and many iterations, we built internal tools to support that work: an ideation tool for structured problem exploration, Spark for early-stage company validation, and Mesh for network and contact management, a nod to Gist, but in a corporate setting. Each one was an attempt to capture what we were learning and make it available to the next team coming through. I’ve been thinking about what this means for AI-era founders for a while.

Along the way, I kept telling founders: find patient, founder-friendly capital with real company-building expertise. Find investors who have built before and understand the journey. Consider the studio model, the co-founder relationship, the institutional support, and the shared methodology. Don’t just take the fastest money. Take the right money and partners.

Practicing what I preach

I’ve been giving that advice for eight years. And now I’m taking it myself.

Lev is a studio company built within PSL, with PSL Ventures and the AI Studio fund as investors, and patient, founder-aligned capital from people who know what early-stage actually looks like. I spent eight years making the case that this is the right way to build. Now I’m doing it.

The tools we built at PSL, the ideation frameworks, the formation processes, and the operational playbooks are genuinely useful. But they only existed inside one studio. Every founder outside PSL had to start from scratch. Every accelerator was reinventing the same programs. Every university innovation lab was running the same ad hoc process. Every corporate innovation team is struggling to get momentum and success.

Let's build Lev

Lev is the attempt to fix that. An AI-powered platform for founders, starting with ideation and validation, growing with teams through formation and operations. Your AI co-founder. The systematic, shareable approach to company building that I’ve spent thirty years developing is available to every founder who needs it. Lev brings togeher 4 product pillars including;
- Canvas - to set and remember context on all the key elements of a startup (e.g. market, cusotmers, product, competitors...)
- Chat - like having a very smart and informed mentor to do the work with the founder, aligned in context with the canvas blocks
- Evaluation - to score each aspect of the company from A-F, helping the founder know where they stand and what to proirtize. Don't wait until your first investor meeting to discover the core strenghts and weaknesses of any idea.
- Tasks - where Lev generates a prioritzed list of the things to work on every week. Focus, progress, momentum.

What I see in AI right now looks more like those early days of website development, Exchange, and spam filtering than most people realize. The foundations have been there for a long time. What’s different now is that the technology is finally accessible enough to change who gets to participate in building companies. Same pattern as the internet. Same pattern as mobile. Bigger stakes.

Thirty years of watching technology change what’s possible for founders. Thirty years of trying to share what I’ve learned. This is what I want to do with it. Find me at getlev.co. Let’s get to work!