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Grow Your Network: Devin Anderson Is A Risk Management Virtuoso
Here's HOW and WHY to connect with Devin Anderson
For years, I've been connecting with interesting people and documenting insights that might help my clients and myself. What was once private is now (mostly) public.
People often ask: "How do you know all these people?" and "How do you connect these (re: random) ideas?" The answer is simple: consistent relationship cultivation and thoughtful note taking. My north star is trusting my instincts, my maps are the constellations in these reflections.
This approach to multidisciplinary networking has helped dozens of clients, colleagues, and friends strengthen their networks and unlock new opportunities. Find my Personal Archive on CultishCreative.com, watch me build a better Personal Network on the Cultish Creative YouTube channel, and listen to Just Press Record on Spotify or Apple Podcasts, and follow me on social media (LinkedIn and X) - now distributed by Epsilon Theory.
You can also check out my work as Managing Director at Sunpointe, as a host on top investment YouTube channel Excess Returns, and as Senior Editor at Perscient.
Feel free to steal these ideas directly - that's what they're for! I can't promise you'll learn FROM me, but I guarantee you can learn something WITH me. Let's go. Count it off: 1-2-3-4!
Introducing... Devin Anderson!
Do you know Devin Anderson? CEO and co-founder of Convexitas, former 15-year veteran of Deutsche Bank's derivatives desk, and a Pittsburgh-born technologist who survived the internet bubble collapse and went on to master Wall Street's most complex financial instruments.
If not, allow me to introduce you. Devin's journey from internet startup bankruptcy to derivatives mastery reads like a financial thriller - complete with FBI raids, bad bank assignments, and lessons learned the hard way about leverage and venture capital. I wanted to connect with him because he embodies something I value deeply: the rare combination of deep technical expertise with hard-earned wisdom about where value truly comes from.
Our conversation is LIVE now on the Epsilon Theory YouTube channel (and this Cultish Creative Playlist). Listen and you'll hear how a Boy Scout from Pittsburgh's South Hills turned early internet experience and an MBA crash course into a derivatives career that survived multiple financial crises.
THREE: That's The Magic Number of Lessons
In the meantime, I wanted to pull THREE KEY LESSONS from my time with Devin to share with you (and drop into my Personal Archive).
Read on and you'll find a quote with a lesson and a reflection you can Take to work with you, Bring home with you, and Leave behind with your legacy.
WORK: Default First, Pay Later
"When you borrow money from a bank, from a loan portfolio - be the first to default, not the last. We thought we were doing the right thing. Like, hey, we could pay - we're gonna pay! That wasn't the right thing to do. The right thing to do was, we should have slammed the bankruptcy right up front."
Key Concept: Devin learned this lesson the hardest way possible during the internet bubble collapse. His company spent two years negotiating forbearance agreements, thinking they were being honorable by continuing to pay. Instead, they became the last valuable asset in the bank's portfolio when everyone else had already defaulted, making them the target for asset seizure. Sometimes being "responsible" in business means making the difficult strategic decision early rather than the honorable tactical decision late.
Personal Archive Note-To-Self: How many times have you drawn out some inevitability because you thought there was a better way to get through it or maybe even around it, even when you were secretly admitting to yourself the whole time that it was inevitable where you - and everybody else in the scenario - would end up?
Devin’s lesson is top of the “easy to say, hard to do” stack. You have a peer group, and you think you’re different. You recognize you’re all in trouble. And you think, and your ego agrees, you’ll be special.
Sometimes there are advantages to admitting you’re wrong first. In the debt financed startup scenario, YES, do it early. But in all sorts of the rest of life too - if you see your peer group and that on average you’re all headed for a mess, once you see it, ACT.
I know my corner of financial services is on track for the slowest motion car crash in customer service history (call it the great wealth transfer or whatever you want). But, even if I was in the middle of realizing it, and moving from what became a big bank backed part to going indie, I got out of the car crash pileup that was forming.
I didn’t top tick it, but I didn’t bottom tick it either, and even without a bust at Devin’s story’s level - the point is, when you and your peer group are all heading for trouble, the only mistake is not to take some action, preferably sooner than later.
Work question for you: When have you continued down a path because it felt "right" even when the strategic indicators suggested a different approach?
LIFE: Value Comes From Cash Flow, Not Stories
"I keep on my desk a framed stock certificate. This was not a public company. This was literally not worth the paper it's printed on. But I keep that on my desk as a reminder of where value comes from. Value doesn't come from a bunch of guys that think that they can buy companies and stick them together and tell people a story. Value comes from cashflow, from operations."
Key Concept: After losing money on private equity shares that became worthless, Devin keeps a physical reminder of the difference between narrative and fundamentals. Whether in business or life, sustainable value comes from what actually works and generates results, not from compelling stories or fancy presentations. This perspective shaped how he built Convexitas - prioritizing profitability and operational efficiency over growth stories and investor backing.
Personal Archive Note-To-Self: Value comes from actions. Extra prior point in that statement. What you do, what you make and not just the signifiers of it, are all that matter.
It’s easy to get fooled by the signifiers of wealth. Stock certificates are such great artifacts in that way. They represent a stake in the business, but they don’t represent the business itself. The business itself is blood, sweat, and tears. And stress, puke, and fears. And joy, pain, and LIFE.
You can live in the land of signifiers. Or you can live in the land of action. When your actions are totally tied to the value, and you accept it, you make big decisions and, if you’re being honest, some money won’t just follow, some meaning will too. That’s priceless. Devin doesn’t stare at that stock cert to this day for nothing.
Life Question For You: What "stories" in your own life might you be prioritizing over the actual fundamentals that create lasting value?
LEGACY: Responsibility Scales With Team Size
"When you start hiring people, I think entrepreneurs are a little too casual with what that means. Zed and I feel like we have a responsibility to Will and Brian, not to blow this up cause it's about more than just Convexitas. It's about their lives too. You have a responsibility to the people that work for you."
Key Concept: Devin's approach to business growth is fundamentally shaped by understanding that employees aren't just resources - they're people with families, mortgages, and career trajectories who chose to trust you with their professional lives. This perspective makes him more conservative about growth strategies and more focused on sustainable business building rather than venture-capital-fueled expansion. It's a mature view of entrepreneurship that prioritizes stewardship over speculation.
Personal Archive Note-To-Self: I had a separate conversation with a mutual friend of mine and Devin’s this week, about the responsibility factor. It ties all the way through to defaulting first and the stock certificates. It’s ties all the way to seeing careers and lives and businesses as living and breathing organisms, with real living and breathing organisms attached to them.
They are trust pacts. They are commitments, to clients and colleagues alike, to do something that works, that’s mutually beneficial, and that won’t let them down unnecessarily. That’s the real pressure of owning and operating a company.
For all the move fast and break things stories, you have to remember lives and legacies are on the line. It’s a breath of fresh air to hear somebody like Devin say this and mean it. It’s also a soul punch for the ages, remembering just how much we put on the line when we invite others to be a part of our ventures.
Take it seriously. It’s a different social pact. We need to talk about entrepreneurship more on this level.
Legacy question for you: How does your sense of responsibility to others influence the risks you're willing to take in your professional life?
BEFORE YOU GO: Be sure to…
Connect with Devin Anderson on LinkedIn
Check out Convexitas for institutional-quality options strategies
Follow Convexitas on LinkedIn for their monthly webinars and derivatives insights
Oh, shoutout to Zed Francis too because, respect. Devin talking about him = immediate follow.
Take a moment to reflect on all these ideas!
You have a Personal Network and a Personal Archive just waiting for you to build them up stronger. Look at your work, look at your life, and look at your legacy - and then, start small in each category. Today it's one person and one reflection. Tomorrow? Who knows what connections you'll create.
Last thing: Don't forget to click reply/click here and tell me who you're adding to your network and why! Plus, if you already have your own Personal Archive too, let me know, I'm creating a database.