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