StarZero All shows Try the podcast clipper →

Sep 24, 2021 · 18m · top-founders

They Help Companies like Fan Duel Stay Compliant, Raising $3m on $150k of ARR

Chris Ultian · 10m spoken Nathan Latka · 5m spoken
0:00 / 0:00

gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

In this interview, Compliable founder Chris Ultian explains how his company pivoted during the pandemic to automate gaming compliance, scaling to $14,000 in monthly recurring revenue and raising a $3 million late-seed round at a $12 million valuation. He details their operator-driven distribution flywheel, cap table management, and the strategic urgency of capturing the expanding U.S. sports betting market.

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Nathan holds 32.8% of the talking time here. How this is scored →

Nathan as informed peer 5.6 Guest teaching 3.0 Guest disagreement 1.8 Nathan pushing back 4.4
05100:0010:000:54–2:57 · Nathan as informed peer 4/10 Introducing Chris Ultian and Compliable's Core Value Proposition Nathan introduces Chris and Compliable, setting up the business model. Chris provides an analogy comparing the software to TurboTax for gaming licensing.2:58–7:33 · Nathan as informed peer 6/10 Pricing Strategy and Revenue Model across Operators and Vendors Nathan presses for specific pricing breakdowns across operators versus vendors and helps synthesize the pivot timeline. Chris explains the dual pricing model and early seed funding.7:33–11:52 · Nathan as informed peer 7/10 Current Traction, Customer Base, and Market Scale Nathan drills deep into valuation mechanics, dilution, and pricing terms across past and present fundraising rounds. Chris clarifies his round structures and explains why they took dilutive capital ahead of market expansion.11:52–14:37 · Nathan as informed peer 6/10 Team Composition and Inbound Operator-Driven Sales Engine Nathan aggressively fact-checks Chris's cap table math regarding founder equity and option pools. Chris clarifies the breakdown between himself, his co-founders, and ESOP.14:38–17:55 · Nathan as informed peer 5/10 Defending Venture Scale vs. Bootstrapping in a Rapidly Opening Market Nathan challenges the necessity of raising high venture multiples on modest ARR instead of bootstrapping. Chris justifies taking venture capital due to the tight time window of state gaming regulation before closing with standard rapid-fire questions.0:54–2:57 · Guest teaching 3/10 Introducing Chris Ultian and Compliable's Core Value Proposition Nathan introduces Chris and Compliable, setting up the business model. Chris provides an analogy comparing the software to TurboTax for gaming licensing.2:58–7:33 · Guest teaching 3/10 Pricing Strategy and Revenue Model across Operators and Vendors Nathan presses for specific pricing breakdowns across operators versus vendors and helps synthesize the pivot timeline. Chris explains the dual pricing model and early seed funding.7:33–11:52 · Guest teaching 3/10 Current Traction, Customer Base, and Market Scale Nathan drills deep into valuation mechanics, dilution, and pricing terms across past and present fundraising rounds. Chris clarifies his round structures and explains why they took dilutive capital ahead of market expansion.11:52–14:37 · Guest teaching 2/10 Team Composition and Inbound Operator-Driven Sales Engine Nathan aggressively fact-checks Chris's cap table math regarding founder equity and option pools. Chris clarifies the breakdown between himself, his co-founders, and ESOP.14:38–17:55 · Guest teaching 4/10 Defending Venture Scale vs. Bootstrapping in a Rapidly Opening Market Nathan challenges the necessity of raising high venture multiples on modest ARR instead of bootstrapping. Chris justifies taking venture capital due to the tight time window of state gaming regulation before closing with standard rapid-fire questions.0:54–2:57 · Guest disagreement 1/10 Introducing Chris Ultian and Compliable's Core Value Proposition Nathan introduces Chris and Compliable, setting up the business model. Chris provides an analogy comparing the software to TurboTax for gaming licensing.2:58–7:33 · Guest disagreement 2/10 Pricing Strategy and Revenue Model across Operators and Vendors Nathan presses for specific pricing breakdowns across operators versus vendors and helps synthesize the pivot timeline. Chris explains the dual pricing model and early seed funding.7:33–11:52 · Guest disagreement 2/10 Current Traction, Customer Base, and Market Scale Nathan drills deep into valuation mechanics, dilution, and pricing terms across past and present fundraising rounds. Chris clarifies his round structures and explains why they took dilutive capital ahead of market expansion.11:52–14:37 · Guest disagreement 2/10 Team Composition and Inbound Operator-Driven Sales Engine Nathan aggressively fact-checks Chris's cap table math regarding founder equity and option pools. Chris clarifies the breakdown between himself, his co-founders, and ESOP.14:38–17:55 · Guest disagreement 2/10 Defending Venture Scale vs. Bootstrapping in a Rapidly Opening Market Nathan challenges the necessity of raising high venture multiples on modest ARR instead of bootstrapping. Chris justifies taking venture capital due to the tight time window of state gaming regulation before closing with standard rapid-fire questions.0:54–2:57 · Nathan pushing back 2/10 Introducing Chris Ultian and Compliable's Core Value Proposition Nathan introduces Chris and Compliable, setting up the business model. Chris provides an analogy comparing the software to TurboTax for gaming licensing.2:58–7:33 · Nathan pushing back 4/10 Pricing Strategy and Revenue Model across Operators and Vendors Nathan presses for specific pricing breakdowns across operators versus vendors and helps synthesize the pivot timeline. Chris explains the dual pricing model and early seed funding.7:33–11:52 · Nathan pushing back 6/10 Current Traction, Customer Base, and Market Scale Nathan drills deep into valuation mechanics, dilution, and pricing terms across past and present fundraising rounds. Chris clarifies his round structures and explains why they took dilutive capital ahead of market expansion.11:52–14:37 · Nathan pushing back 6/10 Team Composition and Inbound Operator-Driven Sales Engine Nathan aggressively fact-checks Chris's cap table math regarding founder equity and option pools. Chris clarifies the breakdown between himself, his co-founders, and ESOP.14:38–17:55 · Nathan pushing back 4/10 Defending Venture Scale vs. Bootstrapping in a Rapidly Opening Market Nathan challenges the necessity of raising high venture multiples on modest ARR instead of bootstrapping. Chris justifies taking venture capital due to the tight time window of state gaming regulation before closing with standard rapid-fire questions.

speaking balance: gold is Nathan, purple is the guest (3 minute bins)

0:00 · Nathan 41.1% · guest 58.9%0:00 · Nathan 41.1% · guest 58.9%3:00 · Nathan 15.7% · guest 84.3%3:00 · Nathan 15.7% · guest 84.3%6:00 · Nathan 36.3% · guest 63.7%6:00 · Nathan 36.3% · guest 63.7%9:00 · Nathan 24.8% · guest 75.2%9:00 · Nathan 24.8% · guest 75.2%12:00 · Nathan 39.3% · guest 60.7%12:00 · Nathan 39.3% · guest 60.7%15:00 · Nathan 30.7% · guest 69.3%15:00 · Nathan 30.7% · guest 69.3%18:00 · Nathan 99.1% · guest 0.9%18:00 · Nathan 99.1% · guest 0.9%
Sharpest disagreement ▶ 13:00 Pushing back on Series A categorization

Chris resists Nathan's characterization of the funding round as a typical Series A, asserting it acts as an opportunistic late seed without traditional investor preferences.

 Hardest push from Nathan ▶ 14:05 Interrogating equity cap table math

Nathan directly challenges Chris's math on founder equity ownership, pointing out that his numbers would leave the co-founders with an improbably small percentage.

 Biggest teaching moment ▶ 15:15 Explaining the urgency of regulatory market windows

Chris educates Nathan on why an emerging regulatory market demands expensive venture capital over bootstrapping to capture first-mover advantage across states.

 Nathan holds their own ▶ 9:20 Rapid calculation of post-money valuations and dilution

Nathan immediately calculates Chris's valuation step-ups and dilution levels on the fly, demonstrating seasoned mastery over SaaS venture financing terms.
the scores for every segment, with the reasoning behind each
ChapterTopicNathan as informed peerGuest teachingGuest disagreementNathan pushing backWhy
Introducing Chris Ultian and Compliable's Core Value Proposition 4312 Nathan introduces Chris and Compliable, setting up the business model. Chris provides an analogy comparing the software to TurboTax for gaming licensing.
Pricing Strategy and Revenue Model across Operators and Vendors 6324 Nathan presses for specific pricing breakdowns across operators versus vendors and helps synthesize the pivot timeline. Chris explains the dual pricing model and early seed funding.
Current Traction, Customer Base, and Market Scale 7326 Nathan drills deep into valuation mechanics, dilution, and pricing terms across past and present fundraising rounds. Chris clarifies his round structures and explains why they took dilutive capital ahead of market expansion.
Team Composition and Inbound Operator-Driven Sales Engine 6226 Nathan aggressively fact-checks Chris's cap table math regarding founder equity and option pools. Chris clarifies the breakdown between himself, his co-founders, and ESOP.
Defending Venture Scale vs. Bootstrapping in a Rapidly Opening Market 5424 Nathan challenges the necessity of raising high venture multiples on modest ARR instead of bootstrapping. Chris justifies taking venture capital due to the tight time window of state gaming regulation before closing with standard rapid-fire questions.

Statements from this episode (13)

Disclosure
Compliable counts sports betting startup Sporttrade as a paying customer
“One of the operators sport trade is the startup in the space. And we're working with another major operator that we can't name publicly yet, but you know those are your sports books.”
Chris Ultian Sep 24, 2021 ▶ 1:55
Disclosure
Compliable charges vendor affiliates $7,000 annually under beta pricing
“So we sell those kind of on an annualized basis 7000 dollars a year is currently our beta pricing for it, and companies that want to work with these sportsbooks pay us that, and that's the annual fee.”
Chris Ultian Sep 24, 2021 ▶ 3:39
Disclosure
Compliable charges major betting operators $5,000 to $10,000 monthly
“So a major operator would probably be around five to 10 K a month for the smaller groups. That's about a thousand a month.”
Chris Ultian Sep 24, 2021 ▶ 4:11
Disclosure
Compliable raised $1.7M post-pivot and nears a $3M round
“So last year on this pivot, after September, we raised 1.7. And we're actually very close to closing another three right now.”
Chris Ultian Sep 24, 2021 ▶ 5:21
Disclosure
Ultian took majority equity for funding early expenses and deferring salary
“When we started this way back when it was on an idea that I had brought in the initial capital and pretty much took no salary in order to make things work while we had a consulting gig that kept the doors open and the lights on, and was able to divert a lot of…”
Chris Ultian Sep 24, 2021 ▶ 6:50
Prediction Not checkable as stated
Ultian predicts US sports betting will consolidate to 50 to 60 operators
“There's going to be like 50, 60 players, total, 20, 30 of substantial size”
Chris Ultian Sep 24, 2021 ▶ 8:00
Disclosure
Compliable secured pilot users in 2020 and booked first revenue in 2021
“September, we didn't have a product. We just had an idea. We got people to sign on to a pilot by November. We had people running through the product. And we actually booked our first revenue July last month.”
Chris Ultian Sep 24, 2021 ▶ 8:54
Disclosure
Compliable raised its $1.7M seed round at a $6.5M pre-money valuation
“The first round right after tech stars was the four million pre money price round. Then we did for the 1.7, that was 6.5.”
Chris Ultian Sep 24, 2021 ▶ 9:51
Prediction Not checkable as stated
Ultian: State licensing infrastructure market opportunity will close in eight months
“If we can get out there ahead of that change, if we can be the provider for the states themselves to be able to grant licenses, that puts us in a pretty unassailable position, and that opportunity will exist for the next six to eight months.”
Chris Ultian Sep 24, 2021 ▶ 11:23
Disclosure
Ultian expects to retain roughly 30% equity after closing $3M round
“I think I'll be at roughly 30%.”
Chris Ultian Sep 24, 2021 ▶ 12:53
Disclosure
Compliable created a 12% employee option pool and has half remaining
“Oh, we started at 12% with last round, and we've been giving it away steadily since, but we have about half of it left, so.”
Chris Ultian Sep 24, 2021 ▶ 13:15
Disclosure
Compliable co-founders collectively own about 15% equity in the company
“So we haven't allocated the full employee options and the co-founders together have about 15 between them right now.”
Chris Ultian Sep 24, 2021 ▶ 14:19
Assertion Not checkable as stated
Compliable is raising capital at a $12M valuation with $160K ARR
“You're at 160,000 dollars in ARR. You're raising a twelve million dollar valuation.”
Nathan Latka Sep 24, 2021 ▶ 14:52
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 2,600 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.

Try the podcast clipper Learn more