Before Money20/20 and the book and NASA, she was busing tables at Ruby Tuesday's in Times Square. Scarlett Sieber graduated from Fordham with an accounting degree she never really wanted, spent a semester abroad in Beijing, came back with one clear realization: "life is short, and accounting is not it.” And then she spent the next year clearing dishes while her classmates climbed the corporate ladder.

Today, she's the Chief Strategy and Growth Officer at Money20/20, the world's largest fintech gathering in three continents, 100+ countries, and the entire global fintech ecosystem in one room. She's a Wiley bestselling author ("Embedded Finance: When Payments Become An Experience"), a Senior Advisor to NASA, a Forbes contributor, a former SVP at BBVA, Chief Innovation Officer at an $8B bank, and one of the most strategically connected people in global finance.

And she got there by doing something almost no one talks about: she stopped trying to get into the room. She built it.

In this episode, Brennan and Scarlett get into all of it: the career origin story most people don't know, the networking philosophy that actually works, what it takes to get on the world's biggest fintech stage, and the honest truth about what innovation looks like from the inside of a massive organization.

What we cover:

→ The real origin story: a small-town Colorado girl, an accounting degree she hated, a semester in Beijing, and a year busing tables in Times Square before any of the titles came

→ Why "owning your unique thing" is your single biggest career weapon, even when you're standing next to a billionaire

→ The #1 networking mistake Scarlett sees constantly: leading with the ask instead of the offer and how to flip it

→ The blunt truth about speaker pitches at major conferences: why your PR agency is probably killing yours (and what to say instead)

→ Why the "5-year plan" might be holding you back and why the most powerful thing you can do is stay flexible

→ What it's really like to be a corporate innovator inside a big institution (hint: lonelier than anyone talks about)

→ Why big banks don't have to move fast and what that should actually teach every fintech founder about how they build

→ The moment Scarlett still comes back to: busing tables at Ruby Tuesday's, looking out those big Times Square windows, and thinking: "I can't believe this is my life. I've made it."

Scarlett Sieber is one of the most deliberately constructed careers in all of financial services. She's never been the product. She builds the room the product lives in. And she came to play on this one.

New episode of Not Another Podcast, out now on YouTube, Spotify, and everywhere you listen.

Most travel companies measure success by bookings. Zach Resnick measures it by how many clients never leave.

Ascend (formerly FlyFlat) is a travel concierge for frequent travelers and it has a 100% 18 month retention rate. Most SaaS companies would die for those numbers. Zach got there by building Ascend around one principle: your time is sacred, full stop.

Before Ascend, Zach played jazz trumpet at Oberlin Conservatory, became a professional poker player, manufactured over $100 million in credit card spend as a college student through Visa gift card arbitrage, and ran Unbounded Capital, a crypto fund built on a contrarian Bitcoin bet that didn't pan out. He then bootstrapped Ascend to over $1M ARR without a single dollar of outside capital and then raised $1.5M from FJ Labs, and eventually brought in Bessemer Venture Partners.

He's a Nassim Taleb disciple. He lives in Lisbon. And he has a rule about red-eye flights that changed how Brennan thinks about his own time.

In this episode, Brennan and Zach go deep on:

→ Why Zach bootstrapped to $1M ARR before talking to VCs, and how to raise from a position of strength instead of desperation

→ How he describes "Delusional chips" as the resource that every contrarian founder needs and how to build it→ The intuition framework: your gut is always right → The red-eye rule and what it actually means to value your own time as a founder

→ Losing his father at 24 and how grief changed his life

→ How Ascend built 94% retention at 12 months with 22-second average response times and 60+ employees

→ The "let it go" framework of when to detach from outcomes and how to know the difference between quitting and releasing

→ The manufactured spend playbook: what opening 300+ credit cards and engineering $100M in spend taught him about systems, edge, and pattern recognition

→ How to interview candidates the way poker players read hands He also shares the one question he asks himself every time he faces a hard decision and why the answer is always already there.

If you're a founder, operator, or anyone who refuses to play someone else's game: this one is for you.

Alfia Ilicheva came to the U.S. at 12 without speaking English, after her father died suddenly. That experience turned into a founder operating system: wake up, look in the mirror, and ask, “Is this the life I want?” She always leads with values and mission-aligment first.

Today she’s the CEO and founder of Formulary Financial, building AI-native fund administration in a world where, according to her, most private market firms quietly run parallel “shadow books” because they don’t trust their administrator’s data. Previously she was a product leader at Bridgewater Associates and the CEO/co-founder of Edna Technologies (incubated inside Apollo). She also co-founded WIN: Women in Innovation and serves on the national board of the Girl Scouts of the USA.

We also get tactical on how she does user research when customers don’t tell the blunt truth, including her “magic wand” question and the difference between functional benefits (data access) and emotional benefits (sounding smart in the meeting).

In this episode:

• The shadow-books reality in private markets

• How to cut through customer theater

• Why “systemization” beats “automation”

• Leadership lessons from Presidents Bush and Clinton

• Her spiciest advice: find where trust is still required

Subscribe for more episodes of Not Another Podcast. If you know someone building in fintech, private markets, or enterprise AI, send them this one.

Ravi Kurani has two exits to his name, and he used both of them as a running start toward harder problems.

As the founder of Sutro, a smart pool chemistry device that he sold to Sani Marc in an acquisition that happened before the product was fully built. And before that, he founded ImpactSpace: the "CrunchBase for impact investing," acquired by ImpactAlpha in 2015. Ravi has lived through the full founder arc twice over. The technical builds, the manufacturing chaos, the emotional weight of handing something you created to someone else, and the strange clarity that comes after.

Now he's doing it again, at a scale that most founders wouldn't attempt: rolling up blue-collar pool service routes through acquisitions as COO of Poolify, while simultaneously building Standard Water Corp as what he calls "the operating system for the water industry."

His thesis, which he's been developing for over a decade, is something he calls the Blue-Collar Billion: the idea that the next massive economic opportunity isn't in another SaaS product or AI wrapper. It's in the physical infrastructure civilization runs on (water systems, service routes, industrial hardware) that Silicon Valley has avoided because the timelines are long, the margins are complicated, and you can't fake progress when the pipes either hold water or they don't.

In this episode, Brennan and Ravi go deep on:

→ The emotional reality of selling a company you built→ The Superhuman PMF methodology→ The first-gen hardware trap→ What Ravi saw in China that convinced him the US is decades behind on physical and digital infrastructure→ Why water is the most underpriced resource on earth→ Selling a startup pre-prototype

This is one for the founders who are tired of the digital hype and ready to think about building something real.

Most e-signature companies charge you to sign a contract. Marty Ringlein is giving it away for free.

Marty is the CEO and co-founder of Agree.com, a fintech-forward agreement platform that collapses the signing → invoicing → payment chain into a single motion and monetizes on the money movement, not the signature. Think Stripe, but the on-ramp is a contract.

This is his fourth company. He's already sold three.

In 2012, he sold nclud's IP to Twitter. In 2017, nvite was acquired by Eventbrite. In 2020, Gather was acquired by Brex. Along the way, he served as a Presidential Innovation Fellow in the Obama White House and started co-teaching product development at Northwestern University, where his core thesis is that product teams should run their roadmaps like venture portfolios: 12 bets, 11 expected failures, and one that changes everything.

He calls it power law thinking applied to product. And it also happens to be exactly how he's building Agree.

In this episode, Brennan and Marty go deep on:

→ Why e-signature should be free forever and how Agree monetizes downstream on payment processing instead of the signature itself

→ The contract-to-cash problem

→ The power law product framework

→ The Eventbrite lesson

→ Why a 7-to-70-person engineering team now does what 7,000 engineers used to do

→ Revenue per employee as the new North Star metric

→ The biggest founder bottleneck

→ The Q4 fundraising strategy

→ Three acquisitions and what repeated "exit + rebuild" does to a founder's psychology

We also play Jenga. And Marty's take on Jenga might be the most accurate description of startup life you'll ever hear.

If you're a founder, builder, operator, or anyone thinking about the future of work in the AI era: this one is for you.

Most startup founders don't make it past year three. Bo Jiang is entering year twelve.

As the CEO and co-founder of Lithic, Bo has lived what feels like two completely different startup journeys in one company. He launched Privacy.com in 2014 as a consumer app helping people create virtual credit cards for safer online shopping. After issuing over 10 million cards, he hit a wall… legacy payment infrastructure couldn't keep up. So Bo did something radical: he built his own modern card processor from scratch.

Then he opened it up to other companies.

That pivot transformed Lithic into an $800M developer platform powering card programs for Mercury, Novo, Parker, and dozens of other next-generation fintechs. Today, Lithic processes over $1 billion in annual transactions and has raised $110M+ from top investors like Bessemer, Index, and Tusk Ventures.

But this conversation isn't about the hockey stick growth or the impressive valuation. It's about what it actually takes to survive and evolve as a founder over more than a decade.

In this episode, Brennan and Bo go deep on:

→ The real story behind Lithic's pivot from B2C to B2B infrastructure (and how other startups literally reverse-engineered their API before they officially launched it)

→ Why Bo believes burnout doesn't come from working hard… it comes from the "messy middle" of trying to control things you can't control

→ How your role as a founder completely transforms as you scale from 3 people to 130+ (and the inflection point where your individual output stops mattering)

→ The mental game of fundraising: why most rejections have nothing to do with you, and how stress literally shows up in your investor Zoom calls

→ Building high-trust, high-context culture while scaling beyond the small team magic of the early days

→ Competing against billion-dollar giants like Marqeta, Stripe, and legacy processors when you're the smaller player

→ Why Bo stayed private and played the long game while everyone else was chasing quick exits during the 2021 fintech boom

→ What it means to be "comfortable with extended periods of uncertainty" – and why that might be the most important founder skill

→ The future of fintech infrastructure: stablecoins, AI agents, and whether physical cards will become relics

Bo is an MIT-trained engineer who spent years building in the unsexy world of payment infrastructure while everyone else chased shiny objects like crypto and neobanks. Turns out, fixing the pipes is where the real, sustainable value lives.

If you're a founder, builder, or anyone playing the long game, this conversation is for you.

Episode Timestamps

0:00 - Intro

1:34 - From Privacy.com to Lithic: building two startups in one decade

5:38 - Consumer vs. B2B

8:23 - How the CEO role changes as the company scales

15:07 - Raising capital without being an AI research lab

19:15 - Generalists vs. specialists

26:28 - Managing mental health & burnout over 12 years

36:43 - Choosing the right investors & advisors

43:06 - War stories: the fraud attack

51:58 - Where fintech infrastructure is headed in the next 5-10 years

Nathan Stoll helped build the modern internet. Literally. He was an early product manager at Google before the IPO. He worked on the systems that powered Google’s ad revenue. He helped scale Google News globally. He even launched Google Suggest: the autocomplete feature billions of people use every day.

And yet… this conversation wasn’t really about tech.

Nathan has built and sold two companies (to Google and Walmart), led product at places like Strava and Handshake, and advised founders for decades. But what he’s thinking about now is deeply counter-cultural in Silicon Valley:

Why emotions, intuition, and human connection matter more than dashboards, models, and optimization.

In this episode of Not Another Podcast, we go deep on the human side of building, the part most founders feel but rarely talk about.

We talk about:

• Why feelings often beat data when making the hardest decisions

• How human networks compound faster than code

• What elite athletics taught Nathan about burnout, pacing, and long-term performance

• Why some of the best founders choose to be less public, not more

• How AI is accelerating faster than our ability to emotionally process it

• The difference between optimizing for conversion vs. optimizing for fulfillment

• Why listening is still the most underrated leadership skill

Nathan also shares deeply personal stories about mentorship, small acts of kindness that changed his life, parenting while building, and why being a “whole human” makes you a better founder.

This is a conversation about building things that last without losing yourself in the process.

🎧 Listen now wherever you get your podcasts.

After 12 years at Forbes, Alex Konrad walked away from one of the most prestigious seats in tech journalism. He ran the Midas List. Co-created the Cloud 100. Wrote cover stories on the biggest names in tech.

And then he left… to build his own media company from scratch.

In this episode, Alex joins me to talk about what happens when you go from covering founders to being one. We get honest about entrepreneurship, attention, media, and why so much of what we glorify in startup culture doesn’t line up with reality.

This conversation isn’t about hype cycles or hot takes. It’s about the actual work.

We talk about why the word “founder” is often over-romanticized, why running a small business deserves more respect than it gets, and why most people misunderstand how press, attention, and storytelling really work. Alex also breaks down what founders consistently get wrong when pitching media, why “nobody cares” is the correct starting assumption, and how to reverse-engineer coverage that actually leads to real outcomes.

If you’re building something in public, thinking about your relationship with attention, or trying to create work that actually holds weight over time, this episode will reframe how you think about all of it.

We cover:• Why entrepreneurship is wildly over-glamorized and what the job actually is• The difference between being a “startup founder” and running a real business• Why “nobody cares” is the most useful mindset for founders and creators• How to think about press strategically instead of emotionally• Why talking to Bloomberg vs an independent outlet leads to completely different outcomes• The real reason founders think journalists are “out to get them”• How AI and content slop are forcing a return to quality and trust• Why some of the best stories look boring right before they look obvious

Listen to the full episode and let us know what resonated.

And if you enjoyed this one, subscribe for more honest conversations about building, pressure, and the unsexy parts of doing meaningful work.

Most founders spend years asking the wrong questions. “How fast can this grow? How big could this be? What’s the smartest next move?”

But the questions that actually shape your life usually come much later… often after you’re already exhausted, anxious, or stuck on a path that doesn’t feel right anymore.

In this episode of Not Another Podcast, Brennan sits down with Evan Walden, CEO and co-founder of Getro (recently acquired by Findem), for a grounded, deeply human conversation about what it really means to build something over the long term.

Evan has spent nearly a decade building companies, mentoring founders, and watching smart, capable people quietly struggle. This isn’t because they weren’t talented, but because they never stopped to ask what they were actually trying to build for themselves.

This episode explores:

• Why companies don’t really die when they run out of money • The difference between keeping something alive through force and building something sustainable• How self-doubt shows up uniquely for entrepreneurs who are creating something from nothing•Why people-pleasing and external validation quietly sabotage founders• The hidden cost of hustle culture and seven-days-a-week thinking• Why taking time off is a signal of strength, not weakness• How values act as a decision-making system when everything feels ambiguous• The idea that every business starts as an art project and the moment when you have to decide what it’s becoming• How to zoom out and ask: Is this still the right thing for me to be working on?

They also talk openly about mental health, therapy, leadership, culture, and the fear many founders carry that if they step away, everything will fall apart. This conversation isn’t about one “right” way to build.

It’s about choosing a game you actually want to play and building something that fits who you are, not just who you think you’re supposed to be.

Most of the AI world is obsessed with chatbots, agents, and software abstractions. Anto Patrex thinks that’s a distraction.

Anto is the founder and CEO of CosmicBrain AI, a former NASA robotics engineer, and an early member of Elon Musk’s xAI team where he helped build Grok. In this episode of Not Another Podcast, Anto makes the case that the real AI revolution won’t live on your screen. It will walk, lift, build, and fight in the physical world. We’re talking humanoid robots today.

In this episode, we talk about why Anto left one of the most coveted roles in AI to bet on humanoid robots, why “physical AI” is advancing faster than most people realize, and how his now-viral Robot Fight Club events ended up convincing skeptical investors and enterprise leaders that robots are far more capable than they thought.

This conversation goes deep into the mechanics and implications of robotics: how robots learn by watching humans, why data and manufacturing matter more than flashy demos, and why China is currently ahead of the U.S. in the robotics race. We also unpack the long-term consequences for jobs, labor markets, national security, and why Anto believes optimism about technology is not naïve, but essential.

If you’re curious where AI is actually headed next, this episode will stretch your imagination and reset your mental model.

In this episode, we cover:

• Why physical AI is a bigger opportunity than chatbots and agents• Anto’s journey from NASA → xAI → founding CosmicBrain• What Elon Musk taught him about constraints, speed, and belief• Why Robot Fight Club wasn’t a gimmick and actually accelerated adoption• The U.S. vs China robotics race and what’s at stake• Why robots won’t kill jobs, but will radically reshape them• How humanoid robots learn skills by watching humans• What the next 5–10 years of robotics could look like

🎙️ Listen now and rethink what “AI” actually means.