When people say no, I say yes.

When there’s a shift/change/whatever-it-is-that-is-happening with technology right now in the economy and the world like the application of LLMs and other tech to everything, once again, I prefer to build.

Taking my own advice, the next chapter of my role in my dayjob is evolving, expanding from CISO to VP Engineering - Platform & Security, continuing to own the CISO responsibilities and taking on some new problem statements! (yay for learning) While leading security is no pushover for a problem statement at any size company, for me, it hasn’t felt right to limit myself to that problem statement, the needs are great in this timeline we’re in - so instead of talking about how the world is changing around me, I just started building so I could be part of the solution, admiring problems was never my favorite past time anyways.

To be clear, I love waxing poetic about the impact of technology on human behavior, economic theory, how the world is changing (or not), and assessing and analyzing that as much or more than the next person. I also feel EXTREMELY responsible to take it upon myself to practice what I preach, to stumble, learn, and fumble with what is new or different to really understand what I’m talking about.

When I started writing Much Potential, I wanted to create an outlet where I could share an ongoing dialogue, create some shared context and understanding, as much as it can spark curiousity in a person, share a perspective that may not be widely held, or challenge an assumption about technology’s role in the world.

Subscribe now

My journey to this point, and my entire career in security are really more about my views and understanding about technology’s role in the world than it is about the technology itself. Every role I’ve ever had, I saw as an opportunity to observe, reflect, experience, and understand the innerworkings of both the technology and the people around me - individually and collectively as a system - it just fascinates me and I never get tired of it!

When I left big companies for startups, I had one thesis - what would it take to build and scale security from scratch, from the earliest stages, Seed, Series A, before you’ve gone too far and settled into your ways. Ultimately, I concluded what felt right for me was that building was the way and everything else that was conventional, “the way it’s been done” in enterprise never made sense. I imagine the large complicated processes in enterprise were meant to reflect the complexity of these environments, but over time, I think the complexity became something we worshiped and not something we managed, something we need to decompose and optimize - not admire.

There are mostly non-technical reasons that have more to do with organizational politics and inertia, human behavior, and relationships for why something is done a certain way in companies, but I wouldn’t dare misrepresent or pretend that if given the option people would want it that way. I mean, come on, WHO LIKES MBRs and QBRs? (Please comment to discuss - would love to learn about the wonders of these rituals)

Prime example: The 10 levels of approvals in ServiceNow, don’t bring me joy (s/o to Marie Kondo).

Some reflection on my journey, I’ve forever chased problems, not titles, working on the right problem > cool title on the wrong problems.

• Long long ago in a galaxy far far away, I wanted desperately to work on improving public education, as a product of K-12 public education - I volunteered with the YMCA, worked in public schools doing IT, ran academic enrichment for elementary students, served on the board of a nonprofit, went to school for poli sci and public policy. Really, I just did as many things as I could in as many ways I could think of in as many ways I was capable to tackle the problem.

• Then cybersecurity (infosec IYKYK) came along, a child hacker I was, I never cared to make computers my career, breaking things, making things, that’s all I cared about, the satisfaction was in the process as much as it was in the outcome, could I get into this network, could I get into this computer, could I get this game to work, mitigations for CVE-2003-0352 aka Blaster Worm for the family PC. One day, I was asked, would you want to come to Washington, D.C. to work on the biggest questions in cyber facing the nation? ABSOLUTELY, I SAID.

• I never felt more purposeful (and tired) working on so many cybersecurity issues in the early innings of national cyber policy. NIST CSF, US-China cyber, federal/state/local coordination, etc. etc. It was a crazy time - extremely controversial back then to propose the notion or concept of reporting requirements for any industry for that matter for anything public company related.

• Expedia Group found their way to me. They asked: Can you help us understand enterprise cyber risk? WELL SURE WHY NOT! Went from responses to members of congress and executive orders to why-do-we-have-so-many-apps (that we wrote), from C to Java, Javascript, Typescript, Scala, Scalatra, C++, .net, Go, whatever, I wish I could say in that order. Spent a whopping 5 years building security from the inside out (really felt like brick by brick), how we understood enterprise cyber risk, how we built and developed cyber capabilities, how we quantified cyber risk liabilities in M&A transactions (rapidly), transforming cyber from service-management to product management, built a super duper massive mega security architecture (to replace all the biggest vendors at the time) with some amazing people (to name a few things), then got tired of it all.

• As the company went through some turmoil at the beginning of this decade, a new problem and with a new question slapped me in the face when the Expedia Group CEO/CFO were unceremoniously let go the morning after a board meeting - How do we build a platform company out of an ecommerce and travel company? SIGN ME UP, I said and joined the Corporate Development team and then went on to lead Commercial Strategy for the Platform Tech group. We did so many things, some things worked, some things didn’t, some things were way ahead of their time, some things - who knows!? We attempted to no less than - re-platform the entire company, re-architect 25+ years of technology, rationalize $10bn+ in acquisitions and mergers, into a massive platform supporting billions and billions of travel consumed annually for a multisided marketplace for hundreds of millions of customers and millions of suppliers.

• After smashing my head against the wall, being humbled by the reluctance to act with urgency in large public companies, a new call came coming from a Series A startup, with new and old problems to solve in new places, the opportunity to ‘travel back in time’ to go back to the beginning, work on security problems again, but now at a startup before they’ve matured into something much scarier? OF COURSE. I didn’t think twice about it (as you can tell), left for a tiny company to build a security program of one. Little ol’ me. We could do it, (mind you pre-LLMs), we’d just take advantage of our relatively small scale to build a security program that focused on outcomes, not ceremony and ritual. I had never worked in startups before, I used to fancy myself a big company problem solver, now I couldn’t get enough of the urgency and clarity being in a tiny company.

• I met the founders of a pre-seed startup and took some time to get to know them, what they were trying to solve and at some point we got to a conversation… Would I consider joining them? It hadn’t crossed my mind, I wasn’t sure, since they were much too early for a CISO. We went back and forth and landed on WHY NOT, there’s no shortage of problems to solve and work on, through a lengthy process of discovery, building shared understanding and context, back and forth with others on the leadership team, the board, we landed on me joining to build the North America Partnerships motion from scratch before taking on the CISO scope as we grew more than 3x/year, many challenges, so much to learn! I had never done partnerships before, but in hindsight, very glad I took the plunge.

So many stories all along the way, so many people I’ve learned so much from - if you ever hangout with me, can talk your ear off with many an entertaining and absurd story.

The journey’s been filled with sidequests too. More to come on that in Pt. 2 and what I’m building and focused on next.

This week you may see a lot of the LinkedIn folk, VCs, and other tech folk alike with posts that say some ChatGPT/Claude/Gemini generated variation of that statement after (not) reading this https://www.anthropic.com/research/labor-market-impacts from Anthropic.

It’s quite an alarming conclusion to make and quite a premature conclusion to make. The essay from Anthropic is not quite as conclusive or fantastical on that dimension and took what I felt was a relatively dry and academic (read: safe) approach to the topic, I suppose they don’t want to alarm anyone (it can’t be helped I suppose).

Few observations I have:

• Over the last 25 years, predictions about the future at best were vague, broad, and captured trends, at best. At worst, their accuracy couldn’t have been more off when there were predictions that automation would lead to a leisure society. Pew Research Center study on how we work way more than ever

• Task expansion over the last 25 years has not been shrinking, it’s been growing, given this, a snapshot in time of what the most common tasks are for any given occupation is extremely limited in its ability to be a predictive tool for a future that also accounts for the developments and changes in work between now and that future. See HBR Article “AI Doesn’t Reduce Work-It Intensifies It”

• Two words: Work Intensification - work overload, work hours, time pressures - everyone wants MORE, everyone wants it NOW. Meta analysis of studies from 1989 to 2022

For my own experience, I can assure you with the advancement of technology, I do not have any less work, if anything, I’ve never had more work, but the demands of work are always for more productivity. Tasks in your profession are like roads, when you automate some, you get new ones, an endless cycle to fill that void with productivity.

What I find is that it is hilarious and absurd that people would spend so much of their time talking about something that has yet to be set in stone in the future that they absolutely are not in an authoritative place to be pontificating about what it will or will not look like.

Do you remember that person at work, pick any one of your jobs, who would complain and complain and complain about a problem, but miraculously never offered any contribution towards solving this problem, never took any initiative. Yelling about this and offering nothing useful merely serves to discourage the people around you from focusing on what they and the people around them can do today to build a better future really is a disservice. Would you say that person is a role model for your company’s employees, for yourself, that this is who we want to lead? Definitely not. That person can please stop/go away/fall in a ditch. Go build something, maybe?

People in the past are horrifically bad at understanding at a granular level in a precise way how we will work and what we will work on. No different than my high school or college counselors not being able to tell me decades ago what I’d be doing today. HOW THE HECK WOULD THEY KNOW. The way things evolve depend on an endless set of factors that have yet to be determined in addition to existing ones that persist. Anyways - don’t waste too much time on those people and their predictions. Those predictions are about as good as me predicting the lottery numbers tomorrow.

Will the continued development and improvements of LLMs and other models change work? Yes. Will some tasks that we do today stop being done by us and begin to be automated partially or entirely? Yes. Has work changed ever in the past and will it change in the future? Yes. Do we have to change how we prepare ourselves and those around us for a world that is changing? Yes. Did we have to do that before LLMs? Yes. Are we supremely awful at it in general and like to put people into rigid roles, job structures, and weird job architectures that take longer to agree on than it takes to improve GPT or Opus? Yes.

Turns out when we build, we expand our thinking, when we expand our thinking, we grow. Humans seemingly have an endless ability to pursue something, I tend to think that “something” is a proxy for purpose, and ideally purpose itself. When we get good at something, we find 5 more things, when we master our current role, we get restless and bored. The job market definitely has evolved in a way that doesn’t seem to let us rest, ¯\_(ツ)_/¯ but who am I to judge. When we pursue purpose though, we continue to push our potential.

We solve problems, we find new ones, we build things, some things last longer, some things don’t, some things were useful, some things weren’t that useful. With each iteration we learn more and more. We fundamentally change and reimagine intentionally or unintentionally everyday we work towards something.

Do I think as a society we’re good at giving people opportunity, not particularly. Do I think we’re good at teaching how to learn instead of teaching a bunch of arbitrarily defined “playbooks” for how to “succeed at life”? No. So there’s a lot of work to do, definitely.

The wisdom people can share are their personal experiences, feelings, and perspective on the human condition. That helps us relate and understand in a way that transcends the superficial differences of our respective eras. I know your high school counselor didn’t look at you and say, “You are going to be a product manager at a B2B SaaS company!”.

There are people all around the world, everyday of our lives, who get no attention, no limelight, no featured guest call on a widely listened to podcast who do incredible things in spite of the limited imaginations of others. Because those with limited imaginations don’t understand how much potential humans have.

Don’t stop imagining.

Don’t stop seeking purpose.

Don’t bet against how much potential humans have.

I love seeing what people are building, I love seeing the imaginations of those out there trying to solve problems, there’s so much energy in it!

Everyone else, you tire me with your pointless points.

Thanks for reading! Subscribe for free to receive new posts and support my work.

When fire was discovered, when the wheel was invented, we didn’t end civilization there.

Don’t be part of the crowd that saw a new wheel and said, that’s it everyone, I’m done. Say it out loud, how can any VC or other self-proclaimed pundit accurately assess the future potential of what is to come without knowing the learnings that compound along the way to that future time. I’ve seen fortune cookies with more imagination. I’m not saying they’re all like that, I’m just saying they’re people too, who can be influenced by things like say, stock price drops that are sudden. Reality-wise most people who have something to lose who see large stock price changes want to seek answers for the direct and indirect consequences that will have on their personal wellbeing.

All this said, something I constantly remind those who are close to me and around me, in personal and profesional settings. You can set goals, you can say, in 5 years I want to be (this thing), remember when you do that, you are implicitly saying you can accurately assess the potential you will have in that timeframe at that future time, which mathematically speaking, you’re not in a position to do well. You will probably directionally get it right, but when you set that goal, you may also be limiting yourself to what you can imagine today. A lot can happen in 5 years, if you choose to start learning something today and work at it for the next 5 years, you’ve just spent half a decade learning and growing. DO you think maybe, just maybe that you will be capable of doing something different at that point than what you’re imagining today? Probably.

Back to the potential of the many, there is so much potential yet to be unleashed on all problems, big and trivial, so many people held back by the limited imagination of their luddite leaders and intellectually recalcitrant boards. The future belongs to those who build, not to those who cower. A better future yet, will be one where we enable companies and organizations of all sizes to solve the problems they are solving - exploring the local maximum of what they can achieve, in a way that wasn’t possible in the last two decades. So much technical talent and resources were hoarded by the few biggest companies in every industry, those companies applied technology in any way they could (both to great failure and to great success), we know what that movie looks like, we’re living in it. We are also seeing the fear in their eyes start to show, we can see the cowering that they are doing, with their RTOs, and their inexplicably backwards thinking in 2026. Their margins are shrinking, their toplines are flat, their AEBITDA isn’t impressive. Their promise of relentless platform-enabled growth with zero marginal transaction costs are being challenged in many ways.

I’ve sat in the meetings, made the annual plans, aligned the stakeholders, convinced the division CFO, company CFO, committee of somebodies and nobodies, big companies had been biding their time, believing they were always one API-first strategy away from glory. Arguing whether their layoffs because of “AI” are real or not, is besides the point, they were going to layoff people for any reason - maybe AI stands for A(ny) I(maginable) reasons.

I can’t wait to see the smallest nonprofits and businesses around my local community take advantage of the changes taking place across the tech industry and seeing how they can better achieve their goals. I can’t wait to see the smartest individuals I’ve ever worked with leave big companies by choice / or not to go build in smaller companies - where TBH - they wanted to go to anyways. The redistribution of building and enabling of builders in so many ways is so much more exciting than the silly narrative that we’re all doomed because we’re going to be TOO productive, TOO capable, have TOO-many things to build. The incredible spinning of the narrative that you should just give up now because no one will need you is intentional, conditioning so you believe you are incapable. It’s easier to sell products exploiting vulnerabilities and fear. If twice as many people were meaningfully able and equipped to solve problems than yesterday, there will be meaningful and material impacts.

Let that sink in, go build something, share it with someone, and get out there (not back to the water coolers of your old bigco job who wants you in office to spontaneously collaborate with remote colleagues in other offices via Zoom calls).

I cannot wait to see what every single laid off employee in the last few years goes on to build. Don’t let dumb dumbs write the future of what you will achieve, you’re going to build great things and we’re all here for it.

If you’re solving problems in 2026 instead of listening to the limited imaginations of the few, lets go build together!

I’m going to be YOLO’ing my thoughts and conversations into Much Potential, a never-ending conversation about helping everyone imagine more.