Last week, I had the privilege of sitting down with
, CTO of Collectors.com, for a Substack Live conversation about the reality of being a tech leader in 2025.What started as a discussion about navigating AI and remote work became something much deeper: a masterclass in human-centered leadership during times of massive transformation.
Dan’s story isn’t your typical Silicon Valley narrative.
It’s one of immigrant resilience, calculated risk-taking, and the kind of thoughtful leadership that prioritizes people alongside profits.
In just 14 months, he helped transform Collectors from an $850 million acquisition into a $4.3 billion valuation; not through aggressive layoffs or flashy technology plays, but through sustainable growth and genuine investment in people.
Here’s what I learned from our conversation, and what you can apply to your own leadership journey.
Tip: Scroll to the bottom for a timestamped outline of our conversation so you can jump to the parts you care about most.
Everything Is Made Up. So Why Not Make It Better?
One of the most liberating things Dan shared was his perspective on change:
“Everything that you have that’s around you, that you do, that you’re living in, was made up by someone or a group of someones. There really is no reason why you couldn’t be and may not be one of those someones to build it for the next generation.”
This mindset comes directly from his parents’ story. As Vietnamese refugees who survived unimaginable hardship: cargo ships, refugee camps, and starting over in a completely foreign country with nothing. They taught him that no professional challenge could ever be as difficult as what they overcame.
But here’s the key: Dan doesn’t let this perspective make him reckless. Instead, it removes the paralyzing fear of the unknown while maintaining respect for the complexity of the work ahead.
Your Takeaway: When facing a daunting change or challenge, ask yourself: “What’s actually at risk here?” Often, our fears are disproportionate to the reality. This doesn’t mean being careless. It means being courageously strategic.
Real M&A Wisdom: Respect What Came Before
When Dan joined Collectors, he found a 35-year-old company with 750 employees and just 22 people in tech. The company was “collapsing under their own success:” outdated technology, manual processes, Post-it notes instead of digital systems.
The easy move would have been to sweep clean and start fresh.
He didn’t do that.
Instead, Dan spent time with each person on the team, understanding their strengths, their institutional knowledge, and their potential. He found people who had been with the company for 25-30 years, an almost unheard-of tenure in tech.
“You never hear about companies that have people stay for that long,” he told me. “That’s a wealth of information and stories and knowledge that you want to tap into if possible.”
His approach was to build career ladders, create clear departments, hire managers who understood enterprise-scale systems, and give people room to grow into specialists rather than remain overwhelmed generalists.
Surprisingly, he retained the majority of the original team through this transformation. Not because he had to, or from fear, but because it aligned with his values and was the smart thing to do.
Your Takeaway: Whether you’re joining a new company or leading a transformation, your first job is to understand what already works and why. The people who’ve been there have context you’ll never have. Your job is to create the structure and tools that give them the chance to thrive. The goal shouldn’t be to retain the team at all costs, but it’s a huge mistake to dismiss without first trying to build with them.
Make Trade-Offs Transparent (But Know Your Audience)
Here’s something Dan admitted publicly for the first time during our conversation: the board was questioning his abilities during that first year.
Revenue wasn’t improving fast enough. He was “exploding the budget” by hiring new people. The backlog was actually getting worse because he was adding process and onboarding people, which took existing team members away from their work.
They were seriously considering replacing him.
What saved him? Clear communication about trade-offs, calibrated to each audience.
For the board, Dan kept explanations high-level: here are the metrics improving, here are the signals to watch for, here’s why sustainable growth matters more than quick fixes.
When they asked about his strangler fig tree pattern for managing tech debt (gradually replacing old systems by building on top of them), he could see their eyes glazing over within 30 seconds. He adjusted: “Just trust me.”
For his team, the opposite was true. Dan practices radical transparency: “I tell them 100% of what I’m going to do, what the plan is.” He wants everyone, from engineers to marketing to HR, to understand the company’s revenue, the reasoning behind decisions, and the trade-offs being made.
This transparency meant his team understood why they were keeping ancient infrastructure in a closet (fire risk, night & weekend work, and more) while investing resources elsewhere. They knew why they couldn’t automate everything immediately. They understood the North Star and could make good decisions without constant oversight.
Your Takeaway: Different stakeholders need different levels of detail. Your board needs confidence in the direction and evidence of progress. Your team needs context to make good daily decisions. Neither is more important. They’re different jobs requiring different information.
The Real Cost of Moving Too Fast
While other companies were doubling and tripling their engineering teams in 2021-2022, (highlighted by Amazon raising their salary cap from $250K to $360K and everyone doing a land grab for talent), Dan grew his team by just 5-10 engineers.
The board questioned this too: “These companies are pulling in thousands, tens of thousands of engineers. You only increased by five or ten engineers. Why is that? Are you incompetent?”
His response?
“I would put a bet that they will all have to course correct how much they’re spending on engineers in the next couple of years... They’re paying high amounts now, but the ROI they’re getting from each engineer won’t match that.”
And yet behind his confident answers, Dan didn’t know for sure. He was trusting his instincts and his common sense. What other companies were doing didn’t make sense. His critical thinking paid off.
He was right. Those companies are now doing 10% layoffs, cutting salaries, and removing benefits. Meanwhile, Collectors continues to grow sustainably, adding salaries and benefits even in today’s economy.
Your Takeaway: Resist the pressure to follow what everyone else is doing just because “that’s what successful companies do.” Sustainable growth (in headcount, in technology adoption, in any transformation) almost always beats rapid scaling. The fast way is often the slow way in disguise.
AI Is a How, Not a What
When I asked Dan about implementing AI, his response was refreshingly pragmatic. He started building an AI department in 2021-2022 with one person whose job was simply to “tinker, experiment, and try a lot of different things.”
Four years later, they released an AI feature in their mobile app that can scan any trading card and identify it within seconds. But it took four years of experimentation to get there.
Meanwhile, his team experiments with 15-30 different AI startups and platforms at any given time. Everything from code generation to automated performance reviews to financial forecasting.
His philosophy?
“AI in general, to me, the way that you should think about it is it’s a how, not the what. It’s not the final goal.”
Some experiments work brilliantly. Dan now uses AI to draft performance reviews that sound exactly like him and are actually less biased than his own first drafts because they don’t suffer from recency bias.
Other experiments fail spectacularly. Ask an AI tool “how much revenue did we have last quarter?” twice, and get two different answers? That’s not ready for production.
The key is that Dan’s team is always experimenting, always learning, always asking: “What problems do we need solved?” first, then exploring whether AI can solve them better than manual processes.
Your takeaway: Don’t adopt AI because you feel you should. Identify the problems you need to solve. Problems that exist whether AI exists or not. Then explore whether AI solves them faster, better, or cheaper. And expect that half your experiments will fail. That’s not a bug; it’s the feature of experimentation.
Fighting for What You Believe In
Near the end of our conversation, I asked Dan what gets him “bent out of shape” at work. His answer was telling:
“The thing that really affects me the most at work is when we aren’t trying to push ourselves to be better.”
He shared an example from last year when the company was considering an expensive acquisition to enter a new business line. Dan believed they could build it themselves, better and faster. His product counterpart disagreed: they didn’t have the time, resources, or priority.
Dan made a bet:
“Give me a month. If you can hold off on that deal for a month, I think I can show enough progress to convince you otherwise.”
He got his month. He gave two engineers a project, a small budget, and a bounty for completion. Within three weeks, they had a working proof of concept. The acquisition was declined. The product they built became hugely successful, generating millions in revenue.
Your Takeaway: Sometimes leadership means putting your conviction on the line. Not recklessly, but strategically. When you deeply believe something is possible, and you’re willing to do the work to prove it, ask for the space to try. The worst case? You learn something valuable. The best case? You create something transformative.
The Why Behind It All
What struck me most about Dan wasn’t his technical acumen or his business results, impressive as they are. It was his clarity about why he does what he does.
He kept coming back to his parents, to the families who sponsored them, to the opportunities he was given.
“I just don’t want to waste it. I want to make sure that I’m making the most of it.”
But his why extends beyond gratitude. He has a vision of what’s possible when we help each other:
“Imagine a world where we’re all helping each other get the maximum... helping everyone to actually be the best version of themselves, how much more fulfilling life could be for each one of us, but also how much better the world could be for all of us.”
This isn’t just feel-good philosophy. It’s the foundation of every decision Dan makes: Will this help people be the best version of themselves? Will this make the world better?
When your why is that clear, the how becomes easier to figure out.
What This Means for Your Leadership
Here’s what I’m taking away from my conversation with Dan, and what I hope you’ll consider for your own leadership:
Reduce fear with perspective. What you’re facing likely isn’t as hard as your mind makes it. Ground yourself in what’s actually at risk.
Invest in the people who are already there. Transformation doesn’t require replacement. It requires structure, clarity, and space to grow.
Make trade-offs explicit and appropriate. Your board doesn’t need implementation details. Your team doesn’t need to be shielded from hard truths. Give each the right level of transparency so they can do their part.
Resist the pressure to move at everyone else’s pace. Sustainable growth beats rapid scaling nearly every time.
Experiment relentlessly with new tools and technologies. But always start with the problem you’re solving, not the shiny new solution.
Put your conviction on the line. Use your own judgment and critical thinking. When you believe something deeply, be courageous and ask for the space to prove it.
Know your why. It’s what will sustain you when the board is questioning you, when the transformation is messy, when the easy path looks tempting.
Dan’s journey from a kid coding games on a TI-82 calculator to a CTO who’s helped build a multi-billion dollar company isn’t just a success story. It’s a blueprint for human-centered leadership in an era of constant change.
The technology will keep evolving. The business models will keep shifting. But the fundamental work of leadership, helping people become the best version of themselves while driving toward a meaningful vision, that remains constant.
Want to connect with Dan? Find him on LinkedIn or visit his website at danvantran.com. And if you’re curious about the world of collectibles and how technology is supporting this thriving community, check out collectors.com to see the innovative work his team is doing.
What resonated most with you from this conversation? Hit reply and let me know. I read every response.
Conversation Topics & Timestamps
Jump to the topics that interest you most:
00:00 - 02:23 - Introduction and Dan’s background overview
02:23 - 04:24 - Why Dan is speaking more and navigating the “weird time” for tech leaders
04:27 - 08:50 - Dan’s family immigration story and his father’s journey into tech/telecommunications
08:50 - 12:50 - How Dan taught himself to code on a TI-82 calculator (and convinced his parents to let him keep it)
12:50 - 15:45 - Getting into trading card collecting and the connection to his sponsor families
15:45 - 19:30 - How Dan discovered Collectors.com and decided to join as CTO
19:30 - 24:30 - The state of Collectors at acquisition: 750 people, 22 in tech, systems “on fire”
24:30 - 27:45 - The approach to transformation: respecting existing talent vs. wholesale replacement
27:45 - 34:20 - How to navigate change you’ve never done before: removing fear, defining “good,” and finding the right experts
34:20 - 37:40 - The importance of getting that first milestone right in change management
37:40 - 44:15 - The board’s concerns during the first year: spending more, moving slower, and nearly being replaced
44:15 - 49:00 - Making strategic trade-offs: keeping infrastructure in a closet, manual on-call, short-term vs. long-term investments
49:00 - 52:15 - Different levels of transparency: what the board needs vs. what your team needs
52:15 - 56:45 - Why Dan only grew by 5-10 engineers while others hired thousands (and why he was right)
56:45 - 1:02:40 - The AI journey: starting with one person in 2021, building to 10-15 engineers, launching card scanning feature after 4 years
1:02:40 - 1:05:30 - Corporate AI experiments: testing 15-30 tools at once, what works (performance reviews) vs. what doesn’t (financial data)
1:05:30 - 1:09:15 - AI as a “how not a what”: always start with the problem, not the technology
1:09:15 - 1:12:30 - What gets Dan bent out of shape: when we stop pushing ourselves to be better
1:12:30 - 1:13:45 - The acquisition bet: convincing leadership to give him one month to build instead of buying
1:13:45 - 1:17:17 - Dan’s “why”: honoring those who helped him and helping others be the best version of themselves
Want more from me?
Substack LIVE Conversations
SAVE THE DATE: Monday, December 22nd at 10am ET for a live conversation with Aamina Awan-Khan about “The Intersection of Identity and Purpose.” Aamina was the former Chief Partnerships Officer in the U.S. Department of State’s Bureau of Public Diplomacy and has held management roles with the Clinton Foundation, the United Nations and Credit Suisse AG. Link to come next week.
If you missed my conversation yesterday with military veteran and philanthropy leader, Maia Molina-Schaefer (
on Substack), stay tuned. I’ll be publishing our full conversation and a written digest next week.Catch up on all of my Substack Lives here.
Work with me in 2026
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May you lead without limits,
