Career Tips from Fintech and Web3 Leaders

What I’d do differently if I were starting my crypto career again (after 4+ years full-time): 1. Take broader exposure: Not reckless trading, but more intentional participation across DeFi, NFTs, RWAs, and other verticals. Coming from traditional finance, I was overly cautious. That limited not just returns - but the depth of my learning. 2. Embrace pivots: Web3 rewards speed, feedback, and iteration. Unless you’re building the next category-defining platform, loyalty to one idea too early often slows you down. Agility is an advantage in this industry. 3. Combat imposter syndrome: In crypto, confidence often precedes credentials. I’ve seen careers built on narrative, positioning, and presence alone. While humility matters, underselling yourself is a liability. 4. Own your narrative: Every participant - chain, project, or individual - represents a story or positioning. The faster you define yours and commit to it, the faster you can capture opportunities. The headline: stay in the game. Crypto continues to be a leading indicator for where the rest of the world is heading. Simply surviving and adapting puts you ahead of the curve.

"Don't let them silence you." This advice, given to Jacqueline Birkel as a young consultant after she was repeatedly interrupted in meetings, changed how she showed up in rooms where she was often the only woman. Yesterday, I shared how Jacqueline transformed her observations of financial struggles into round, a FinTech startup serving beauty and wellness entrepreneurs. Today, I’m sharing the leadership insights she’s gained that stayed with me long after our conversation. After building her career at Accenture, JPMorganChase, and American Express, Jacqueline faced the challenges of being a female founder in FinTech. Her experiences shaped a leadership philosophy balancing authenticity with impact: 1. "Take feedback as a gift. If someone cares enough to share observations about how you can improve, that's invaluable. But you have to create an environment where people feel safe doing so." 2. "Question the standard playbook. When investors suggested traditional Silicon Valley methods, I explained our why – we're building for beauty and wellness entrepreneurs, many of whom are women, people of color, and multilingual. Our approach needs to reflect that, and our perspective gives us insights others might miss." 3. “Authenticity beats formality.” Early in her career, Jacqueline thought leadership meant formal suits and emails. “I realized people do their best work when they have information and feel seen, not when you're wearing a blazer. Being my authentic self made leadership sustainable.” 4. "Build genuine connections and relationships. When you find someone you connect with through projects, volunteering, or community work, exchange information and stay in touch. It shouldn't feel laborious because you're connecting with people you genuinely like. That’s how we secured our first investor – one ask, one check." 5. “Location can be strategic.” Building between Chicago and Atlanta rather than Silicon Valley was deliberate: “Building outside traditional tech hubs makes you stand out. You become a big fish in a smaller pond, which is validating when you’re early-stage.” The insight that resonated with me most was Jacqueline’s core belief: “Why not us? The only difference between someone who’s built something and someone with an idea is taking action. If you don’t take that leap, someone else might do it instead.” As a woman who’s built her own business, I found myself nodding vigorously. Every successful venture begins not with certainty but with someone brave enough to ask, “Why not me?” and take that first small step. What leadership convention are you following that might not serve your authentic self? How might embracing your unique perspective become your greatest strength? Repost if you're inspired. Tag someone who needs to read Jacqueline’s story. ---------- This post is part of my ongoing LinkedIn series featuring inspiring women leaders who are making an impact in business and life. Follow me for more remarkable stories. 

I spoke with 25 finance leaders at thriving startups. Different journeys—same mindset. Here’s what they all had in common: They don't chase titles. They chase impact. Every single one joined companies doing less than $10M in revenue. All were the first finance hire. Some walked into complete chaos—no systems, no processes, just spreadsheets scattered all over Google Drive. But here's what struck me: they all lit up talking about it. Not one regretted leaving the comfort of Goldman Sachs or McKinsey. Not one missed the prestige. Because they found something better—the rush of building from zero. The patterns were impossible to ignore: 1️⃣ They think in systems, not tasks. One leader told me: "I don't reconcile accounts. I build reconciliation systems that scale." Another said: "My job isn't to close the books—it's to design a close that takes 3 days, not 3 weeks." 2️⃣ They measure success differently. No one mentioned their title progression. Instead, they talked about the sales comp plan that unlocked growth. The data warehouse that gave everyone visibility. The forecast model that helped raise Series B. 3️⃣ They speak business, not accounting. They don't say "we need better accruals." They say "we're leaving money on the table because we can't see our unit economics." They translate finance into growth. 4️⃣ They're allergic to maintenance mode. One VP told me: "The moment I'm just keeping the lights on, I know it's time to go." They need the intellectual challenge of solving new problems, not managing solved ones. 5️⃣ They know when to leave. This surprised me most. Every builder had a clear exit criteria: "When the business runs without me." "When sale is the next milestone." Then they hand it off and find the next challenge. But the biggest commonality? They all struggled with the same doubt: "Am I hurting my career by not climbing the ladder?" Until they realized—they weren't avoiding the ladder. They were building their own. One head of finance put it perfectly: "I've built finance functions at 3 companies. Each time, I start stronger. I see patterns faster. I build better systems. That's my competitive edge." The builder's path isn't for everyone. It's messy. It's thankless at times. You won't get the CFO title at 35. But you'll get something else: the deep satisfaction of turning chaos into clarity. Of building something that lasts. Of knowing that every system, every process, every insight you created—still runs today. If you're in finance and feel stuck in maintenance mode, maybe it's time to build something new. The best time to join a startup? When finance is still broken. That's where builders thrive.

Everyone talks about Musk, Thiel, and the PayPal Mafia. But they all needed one Ukrainian genius to make it work... Max Levchin arrived in the US at the age of 16 from Ukraine. His obsession with computers led him to build PayPal's core tech & grow Affirm into a $24 billion giant. Here's what we can learn from him: 1. Embrace Failure "The first company I started failed with a great bang. The second failed a little less, but still failed." But despite each failure, Levchin kept building until he struck gold with PayPal. See failures as stepping stones to success. 2. Take Risks Early Levchin started multiple companies in his early 20s. His logic: Young founders have nothing to lose – that's a big advantage. You can always fall back on traditional careers later. But you'll never be more free to take big swings than when you're young. 3. Choose Partners Who Push You "Find a partner you'll try to impress daily & one who will try to impress you" This philosophy led him to Peter Thiel first & Elon Musk later for PayPal. Together they changed finance forever. 4. Focus On Your Strengths After PayPal, Levchin tried diversifying away from fintech. But that was a mistake. He realized he was happiest solving financial problems. So he returned to fintech & built Affirm into a $24 billion giant. Stay in your zone of genius. 5. Trust Your Instincts "Whenever there is any doubt, there is no doubt." Your gut feeling is usually right. If something feels off, it probably is. Don't waste time second-guessing clear internal signals. 6. Solve Hard Problems When PayPal faced devastating credit card fraud, most wanted to give up. But Levchin's response? "Man up & solve it." He created fraud detection systems that made online payments possible. The harder the problem, the bigger the opportunity. 7. Build Elite Teams Levchin is a core believer in people. He says that great teams can pivot to find success. Bad ones will fail even with a perfect market. 8. Be Ruthlessly Honest During layoffs & hard times, Levchin preaches honesty over everything else. Although it hurts in the moment, dishonesty destroys forever. Within a team, truth is the foundation of trust. 9. Never Stop Learning Even after billions in exits, Levchin still codes. He calls it "pure magic" and stays hands-on with technical problems. Most founders get rich & disconnect from their craft. Levchin got rich & doubled down on his passion. 10. Stay Humble While his PayPal co-founders became celebrities, Levchin focused on the future of finance. Sometimes the biggest innovators aren't the ones making the most noise. They're the ones solving the hardest problems behind the scenes. - I'm Winston Zin - CEO, founder, and tech & fitness enthusiast: • Follow @winston_zin for more startup insights • Join the revolution in AI-powered fitness: Impakt.com • Share this thread to spread the revolution ♻️ The future of fitness is intelligent.

The Brex / Capital One $5.15Bn acquisition is a huge deal and should be celebrated. How did they do it? I've studied their culture by interviewing Henrique Dubugras (Co-founder), Michael B. Tannenbaum (ex-CFO, Employee #1), and Art L. (CBO, Employee #50). These are 10 important lessons I learned from them. Henrique and Pedro built Brex as teenagers from a house in SF to a generational fintech in 9 years. From a startup card to $100B+ in TPV. Along the way, they created a culture that has already spun out dozens of founders who have raised over $800M+. Here's what I learned on our Fintech Leaders episodes: 1. Your first 10 leadership hires matter more than your first 10 employees. Those leaders create processes and structures that outlast them. Some of Brex's first 10 employees didn't become managers, but the leaders they hired early shaped the culture. 2. Great founders get lucky with great mentors. Henrique's first investor was a payments founder who taught him the entire industry before he really understood it. The right early backer can accelerate your learning curve dramatically. 3. Build everything in-house. A major competitive advantage came from building all their software from scratch. Brex built their own issuer processor because Marqeta and Stripe Issuing were not mature when they launched. That proprietary infrastructure enabled deeper integrations than competitors could ever achieve. 4. Your best culture exists in the edges, not the nodes. Henrique used to think companies were 100% about the people. Now he believes the real value is in the processes, systems, and structures people create. Great companies can survive personnel changes because excellence lives in the connections between people. 5. If you have five priorities, you have zero. Every employee and team has a single OKR. The discipline of extreme focus brought them back to hyper growth after a period of growing pains. 6. Move at an unnaturally fast rate. When someone says they will revert next week, ask why not tomorrow. Analysis paralysis kills momentum. Brex leaders operate with urgency that feels uncomfortable to most people. 7. Listen to your customers. Brex built partnerships with Navan and Zip because 87 customers asked about Navan integration in six months. The biggest strategic moves came directly from customer requests. 8. Land and expand is crucial in enterprise. Large customers do not deploy new vendors to everyone at once. They want to try you in one use-case first. Brex restructured sales comp with longer hold periods so reps would land small and expand later. 9. Promoting from within creates loyalty. Behind every internal promotion, a manager is taking a risk on you. The easiest path is always hiring someone who has done the job before. Backing internal talent is harder but builds something lasting. 10. Dream big is not a cliche. Their audacious goal-setting culture produced a generational company in 9 years. Bravo! Link in comments ⤵️