Sara Croft and Christian Beck, co-founders of Five Four, join Paul Anthony to talk about running an on-demand marketing and design agency for early-stage startups. Sara spent years in-house, including at a nonprofit that supported Indiana tech companies, before landing at an agency where Christian hired her as head of marketing. Christian started as an in-house UX designer at Autodesk and later realized he cared more about design than the industry he was designing for. Five Four also built OpStart's brand, and now uses OpStart for accounting.

Both wanted to put their skills to work for founders rather than for a single product. Sara says working across many companies gives an agency a volume of reps an in-house team never gets. They explain why they want clients to outgrow them and hire full-time staff, and they get candid about firing clients, tying every engagement to a result like revenue, and saying no when the fit is wrong.

From there they get practical: how to shop for an agency, why founders have to keep selling while marketing gets off the ground, and how to think about a marketing budget. Christian explains why he builds client sites with AI but won't let it write the words, and Paul adds his view on why AI still needs an expert holding the reins. They close with advice for new founders: be ready to sell, and be open to a co-founder.

In this episode, you'll learn:

● Why Five Four ties every engagement to a result, and why Sara treats a prospect who can't say what they want from marketing as a warning sign

● Why they want clients to graduate to in-house hires, and why they have fired more clients than they expected

● How to shop for an agency by writing your own brief first, and why marketing specialists work like doctors

● Why early-stage marketing runs on a cycle of asking whether the audience, channel, and message are still right, anywhere from every three months to every six

● Why founders still have to sell, and why talking to buyers beats analytics for testing a message

● Why setting a goal before trying a channel, like a podcast, is the only way to know if it failed

● Why Paul says companies that raise money tend to underspend on growth, and how a marketing hire's salary can eat the entire budget

● Why Christian calls AI backwards looking and average, and how he still builds client sites with it, from Figma designs to Claude Code to Webflow

Timestamps

00:00 - Meet Sara Croft and Christian Beck of Five Four

03:12 - From in-house marketing to starting an agency

07:28 - Christian's path from UX designer to agency owner

11:41 - Letting clients graduate instead of locking them in

13:30 - What makes Five Four different

21:14 - Firing clients to protect your reputation

22:28 - How to choose an agency, starting with your brief

27:27 - Product market fit, then channel fit

31:02 - How long to give a marketing experiment

33:42 - Why founders still have to sell

41:52 - Start with a goal, not a tactic

45:04 - Marketing budget mistakes

47:08 - What AI can and can't do for marketing

1:01:19 - The most common early-stage marketing mistake

1:03:53 - Advice for anyone starting a business

Connect:

● OpStart: https://www.opstart.co

● Paul Anthony on LinkedIn: https://www.linkedin.com/in/paul-anthony-8a256087/

● Sara Croft on LinkedIn: https://www.linkedin.com/in/saracroft/

● Christian Beck on LinkedIn: https://www.linkedin.com/in/christianmbeck/

● Five Four: https://fivefour.partners

● Five Four on LinkedIn: https://www.linkedin.com/company/five-four-partners/

Hashtags: #OpStart #FiveFour #StartupMarketing #EarlyStageStartups #B2BMarketing #MarketingAgency #BrandStrategy #StartupSales #StartupGrowth #AIandMarketing #Indianapolis #StartupPodcast #FounderStory #Entrepreneurship #FoundersJourney

Liam Redmond joins Paul Anthony to talk about building Yelo, the ride and nightlife discovery platform he started as a Notre Dame undergrad and now runs full time from New York. Liam graduated in 2025 and has already been named to Forbes 30 Under 30. He describes the founder path in blunt terms, comparing it to chewing glass, but says it's a career he wouldn't trade.

Yelo began as a lunchline conversation about Uber costs and grew into a student exclusive rideshare, paying drivers the full fare and undercutting Uber and Lyft by 30 to 40 percent. Liam explains how watching the ride data revealed something Uber's data never could: nearly all of Yelo's rides ended at bars, clubs, and house parties, which pointed toward a nightlife discovery business rather than a straight rideshare play. That insight turned into promoting venues directly, including one campus concert that pulled 600 people in line for a room built for 300.

Now a year out of college and building full time in New York, Liam talks through why he thinks autonomous vehicles help Yelo more than they threaten it, how the team vets venues to protect rider trust, and why keeping the founding team young, with a head of growth who's 19, is a genuine edge rather than a liability. The conversation closes on what Liam calls the "hustle slop" glamorizing founder life online, and the more honest advice he gives friends who ask if they should start a company.

In this episode, you'll learn:

● Why Yelo started as a "student exclusive Uber" that paid drivers 100 percent of the fare

● How a group chat splitting Uber costs became Yelo's first mobile app

● The data insight that ride bookings, not check-ins, are the truest signal of where people are actually going

● How one concert venue promotion turned into 600 kids in line for a 300 person room

● Why Liam believes autonomous vehicles help Yelo's business instead of threatening it

● How Yelo vets venues and uses rider feedback before promoting a business to the wider platform

● Why Liam thinks a 21-year-old founding team is now an advantage, and what he tells students asking about becoming a founder

Timestamps

00:00 - Welcome and introducing Liam Redmond

01:01 - From pre-med dreams to a Notre Dame founder

02:46 - Building a "student exclusive Uber" from a lunch line

04:09 - Raising a friends and family round as undergrads

06:00 - The insight: ride data reveals where the party is

07:52 - Turning ride data into a venue promotion engine

09:17 - The viral moment: 600 kids outside one venue

11:03 - New York, and competing without competing on rides

14:04 - Autonomous vehicles and the DoorDash data parallel

17:20 - Vetting venues without losing rider trust

20:04 - Scaling beyond EDU emails and zero CAC

22:09 - "Hustle slop," and why founders feel so alone

28:15 - The 21-year-old team, New York, and what's next

Connect:

● OpStart: https://www.opstart.co

● Paul Anthony on LinkedIn: https://www.linkedin.com/in/paul-anthony-8a256087/

● Liam Redmond on LinkedIn: https://www.linkedin.com/in/liam-redmond/

● Yelo: https://joinyelo.com/

Hashtags: #OpStart #Yelo #Rideshare #NotreDame #Forbes30Under30 #StartupPodcast #FounderStory #Entrepreneurship #FoundersJourney #GenZ #ConsumerTech #NewYorkStartups #Marketplace #VentureCapital

Neha Govindraj, founder of Bonside, joins Paul Anthony to trace a path that runs from Bain and Company's consumer and private equity practice to the operator seat at Glowbar, the 30-minute facial concept she started in New York and grew to about 30 locations across the East Coast. Running that business is where she saw how strong brick-and-mortar retail can be, and how few resources exist around it.

The idea for Bonside came out of a deal she structured for herself. Traditional debt sat on one end of the market, with personal guarantees, covenants and six-month processes. Venture equity sat on the other. Neither fit a small-footprint model built to open 10 or 20 doors a year. So she built her own revenue-share agreement, then noticed she felt nervous telling other founders about it. That was the signal: keep it as a secret weapon, or build a company and put it in everyone's hands.

Bonside now writes checks from $25K up past $5M, repaid as a fixed percentage of monthly revenue, almost always under 10%, until a set return is met. Underwriting runs on models trained on Bonside's own past decisions and the outcomes attached to them. The conversation closes on which problems a founder should actually solve themselves, why resilience matters more than runway, and the $60,000 payroll tax credit Neha almost never got back.

In this episode, you'll learn:

● How Bonside structures capital as a fixed share of monthly revenue instead of a fixed payment or an equity stake

● Why check sizes run from $25K to $5M and why opening new doors is the number one use case

● The two datasets behind Bonside's underwriting engine, and variables like four-wall EBITDA at location two and revenue standard deviation across locations

● The math that made the market obvious: roughly five VC funds writing about three brick-and-mortar checks a year

● Why Neha spent early money on brand identity and design, a call most fintech founders would not make

● How raising debt differs from raising venture, and why a no from a debt fund is more useful feedback

● Why one operator took capital from Bonside five times and still owns 100% of the business

● The $60,000 payroll tax credit that was written off as an IRS delay, and how it came back in six weeks

Timestamps

00:00 - Intro

01:17 - From Bain to Founding Glowbar

02:23 - How Bonside Structures Capital

04:14 - The Hybrid of Debt and Equity

05:11 - Inside the AI Underwriting Engine

06:57 - The Deal That Became a Company

08:44 - Growing With One Operator Across Five Checks

11:15 - Raising Debt vs Raising Venture

13:35 - Why Bonside Invested in Brand First

17:05 - The Operator Seat: Retail vs Fintech

19:02 - How Badly Do You Want It

21:25 - The $60K Tax Credit Fight

25:10 - What to Outsource, and Where AI Stops

Connect:

● OpStart: https://www.opstart.co

● Paul Anthony on LinkedIn: https://www.linkedin.com/in/paul-anthony-8a256087/

● Neha Govindraj on LinkedIn: [ADD URL]

● Bonside: https://www.bonside.com

Hashtags: #OpStart #Bonside #BrickAndMortar #RevenueBasedFinancing #Fintech #RetailGrowth #StartupFinance #VentureCapital #FounderStory #StartupPodcast #Entrepreneurship #FoundersJourney #NYCStartups #AlternativeFinancing

Alex Kruszewski, Founder and CEO of Abacus, joins Paul Anthony for a homecoming conversation that traces an unlikely path from investment banking to building what he calls a brand-new category in wealth technology. A Notre Dame finance graduate, Alex began his career in investment banking and private equity at firms including Evercore, Madison Dearborn Partners, and BDT, before a step into pharmaceutical operations turned into a sale process that ended with Eli Lilly buying the business. That outcome led the founding family to ask him to stand up Goldfinch Capital Partners, a Chicago-based family office where, at 27, he served as CIO running the investments.

It was there that Alex hit the problem that would become Abacus. Everyone talks about allocating capital, he explains, but almost no one talks about the unglamorous work of tracking it. At Goldfinch, answering the deceptively simple question of "what are we worth right now?" required six-figure legacy software plus two full-time accountants, and it was only ever as accurate as the last person to key in the numbers. Abacus fuses software and service to solve that garbage-in, garbage-out problem, building each client a "financial digital key" that ports in public equities, private equity, venture, real estate, debt, and documents, then keeps it continuously correct through a White Glove services team of ex-bankers and private equity professionals working alongside agentic AI.

Paul and Alex dig into the model Abacus calls SPaaS, service presented as a software: clients get the interface without ever having to fill it in. From there the conversation opens up into pricing philosophy in an AUM-obsessed industry, why Abacus deliberately stayed in stealth, and a genuinely useful stretch on team building, incentives, and founder life with young kids. Alex closes with contrarian advice that cuts against startup culture: don't do it for the money or the title, and don't do it at all unless the vision is so big it's the only thing you can work on.

Key Takeaways

● Allocating capital gets all the attention, but tracking it is the real unsolved problem, and it only stays accurate if the underlying labor is flawless

● Abacus builds each client a "financial digital key" that consolidates every asset class and document, then permissions it out to advisors, CPAs, or AI tools on demand

● The SPaaS model (service presented as a software) delivers the interface without making clients do the data entry, pairing agentic AI with human domain experts

● Alternatives resist standardization, so human relationships and domain expertise, not just API pipes, are what actually keep the data current

● The best AI use case is not replacing people but freeing them from the annoying parts of their jobs so they get back to the work they were hired to do

● Great teams come from defining a narrow scope, identifying what makes each person tick, and incentivizing them accordingly, not from hiring generalists

Connect:

● OpStart: https://www.opstart.co

● Paul Anthony on LinkedIn: https://www.linkedin.com/in/paul-anthony-8a256087/

● Alex Kruszewski on LinkedIn: https://www.linkedin.com/in/alex-kru/

● Abacus: https://www.abacuswt.com

Hashtags:

#OpStart #Abacus #WealthTech #FamilyOffice #StartupPodcast #FounderStory #FinTech #ServiceAsSoftware #SPaaS #SmallBusiness #StartupLife #Entrepreneurship #AI #FoundersJourney #PrivateEquity

In this episode, we sit down with Tyler Bliha, founder of Abode Money, to unpack how he’s building an AI-powered financial manager for homeowners.

Tyler shares his journey from investment banking and private equity to early-stage fintech, and how his experience at UpEquity helped shape the vision behind Abode Money. We also dive into why homeowners are often overspending on property taxes, insurance, and other recurring housing costs — and how Abode is using AI to simplify and automate savings.

We discuss:

• Why property taxes are the perfect wedge into the homeowner financial relationship

• How Abode expanded from Texas to all 50 states

• The role of AI in automating complex, localized financial workflows

• Why founder-led fundraising requires urgency, process, and signal

• What makes homeownership one of the biggest untapped opportunities in consumer fintech

Guest: Tyler Bliha, Founder, Abode Money

🌐 Abode Money: abodemoney.com

Dr. Avi Jayaraman, physician, two-time founder, and CEO of Blue Light Health, joins Paul Anthony in the studio to talk about building healthcare businesses that actually get paid for. Avi went from earning his MD in Dallas to accidentally falling into startups with Sonara, a platform that let opioid-recovery patients take methadone at home instead of traveling to a clinic every single day.

After Wharton and a stint on the VC side, the founder seat pulled him back in. Blue Light Health is his virtual clinic taking on something close to home for a lot of parents: technology and social media addiction in kids. Avi breaks down the staggering numbers behind the problem and why a clinical approach beats a tech-only blocking app.

He and Paul close on the lessons every founder needs: when to go straight to enterprise decision-makers, why the right angel investors change everything, and practical advice for keeping your own kids out of a clinic down the road.

In this episode, you'll learn:

● Why the biggest opportunities come from picking a huge problem and catching a lucky confluence of timing factors

● How a few well-connected angel investors unlocked enterprise sales conversations Avi never could have reached on his own

● The case for going straight to the board, CEO, and CFO instead of testing your product in a small, controlled setting first

● Why technology and social media addiction in kids is a clinical problem, not a "use a blocking app" problem

● How existing psychiatric medications and therapy can address both the addiction and the underlying mental health disorder

● Why building the clinical science first is the real moat, and how that data unlocks value-based-care contracts with payers

● How AI is collapsing the old choice between building tech or providing a service into a single venture-scale model

● Avi's advice for parents on delaying screens and protecting kids' emotional regulation early

Timestamps

00:00 - Welcome and meeting Dr. Avi Jayaraman

01:12 - Avi's background: from med school to founder

02:00 - Sonara: at-home methadone and access to care

12:00 - Picking big problems and catching the right timing

12:39 - Finding room for the right angel investors

13:48 - Going straight to enterprise decision-makers

17:41 - Private equity in healthcare: the other side

20:46 - Blue Light Health and the gap on the clinical side

22:33 - Why screen addiction in kids is a clinical problem

24:16 - Therapy and medication for digital addiction

28:00 - Building a venture-scale business that's profitable early

34:08 - The team and tech behind Blue Light Health

36:51 - Proving ROI to insurance payers

40:20 - Where tech fits and the real moat

45:55 - Advice for parents on kids and screens

49:30 - How to support Blue Light Health

50:42 - Closing: the role OpStart plays behind the scenes

Connect:

● OpStart: https://www.opstart.co

● Paul Anthony on LinkedIn: https://www.linkedin.com/in/paul-anthony-8a256087/

● Dr. Avi Jayaraman on LinkedIn: https://www.linkedin.com/in/avinash-jayaraman/

● Blue Light Health: https://bluelighthealth.com

Hashtags: #OpStart #BlueLightHealth #HealthcareStartups #StartupPodcast #FounderStory #DigitalHealth #MentalHealth #ScreenTimeAddiction #VentureCapital #StartupFunding #HealthTech #Wharton #FoundersJourney #Entrepreneurship #StartupLife

In this episode, we sit down with Tommy Flaim, founder of Silly Pickles, to unpack how he built one of the fastest-growing adult rec sports communities in the country.

Tommy shares his journey from investment banking to launching (and winding down) his first startup, and how he stumbled into building a scalable, software-powered league model that’s now live in 65+ cities.

We discuss:

• Why most adult rec leagues fail to attract young professionals

• How Silly Pickles scaled to a $3.4M run rate in 18 months

• The franchise-style operating model behind 100+ facility partners

• Raising capital while building custom software from scratch

• What founders should know before quitting their job

Guest: Tommy Flaim, Founder, Silly Pickles

🌐 Silly Pickles: sillypickles.com

Greg Slauson, CEO of Proper Voltage, joins Paul Anthony to unpack how a career that started selling structured fixed income on a Goldman Sachs trading floor led him through a solar fintech rocketship, a caramel apple business bought with an SBA loan, and ultimately to building the intelligence layer that turns batteries from a limiter into an enhancer. Greg and Paul have been friends for 12 years, since they were randomly paired as summer intern roommates in Chicago, and Proper Voltage runs its accounting and tax through OpStart, so the conversation moves easily between deep technical detail and the real mechanics of building a company.

From there the conversation works through a founder's education the hard way: growing a capital markets team from two people to mid-twenties at GoodLeap, buying and operating Daffy Apple while juggling two other jobs at 90-hour weeks, and learning that a 40-year-old running an HVAC business often knows more than a fresh MBA. Greg is candid about why he walked away from fintech entirely, why he believes the back half of the 2020s belongs to hardware, and how that thesis led him to a six-person battery startup he convinced to hire him.

The result is Proper Voltage, the battery operating system that digitally adjusts voltage so products get full power through the entire discharge, enables new chemistries to plug into existing systems, and unlocks features like hot-swapping for robots and data centers. Greg and Paul close on the parts most founders underrate: why working capital is the lifeblood of a hardware business, why chasing headline revenue numbers can quietly kill you, and why the little things, down to whether a deck says Q1 or Q2, compound into trust.

In this episode, you'll learn:

- Why Greg optimized his early career around who he worked for instead of salary or title, and how that compounded over 12 years

- What buying and running a seasonal caramel apple business taught him that 90% transfers to companies of any size

- How Proper Voltage turns a battery from a product's limiter into its enhancer, explained through a power drill, a drone, and a Boston Dynamics backflip

- Why Greg believes humanoid robotics in 2026 looks like AI did in 2021, and what that means for the next three years

- How sodium-ion batteries change the safety and economics of data center backup power

- Why working capital, not just margin, determines how far a hardware company can scale without giving away equity

- The case for building slow and steady when VCs are pushing for zero-to-$60M in a year