Sunroof

Travis brought hard-won lessons from his first exit to his new venture. His previous company, launched in 2011, grew to over $6 million in revenue by targeting hedge funds and private equity firms with alternative data research. He raised about $10 million across multiple rounds (including a $7 million round at a $30 million valuation in 2018) and exited in November 2019 with a 33% equity stake. While not "FU money," the exit gave him capital and insights to try again.

The first company taught him painful lessons about market selection. His clients—sophisticated financial institutions—were willing to pay quickly but also willing to move on to the next hot thing. Once too many competitors had access to the same data, everyone lost their competitive edge. That fragmentation and the clients' fickle nature made scaling difficult. He realized he wanted a stickier market with deeper, recurring relationships.

Travis launched Sunroof in 2020, targeting a vastly different market: banks and mortgage lenders. Instead of selling alternative data to hedge funds, he built a SaaS platform addressing three core problems in the lending space: customer experience (survey data, performance analytics), employee experience (internal metrics and feedback), and online reputation management (encouraging reviews and reputation building).

He bootstrapped the company with over $250,000 of his own money and kept it lean. The team started small—just five full-time employees, three of them engineers. Travis handled business, sales, and marketing while staying involved enough to understand the engineering without trying to lead it. He used Airtable as a key tool for building and organizing the product.

Travis went direct to banks with a subscription model rather than a revenue-share arrangement. The pricing strategy reflected the fragmented nature of the market: customers could buy one, two, or all three modules (customer experience, employee experience, ORM), with prices ranging from $4,000 to $12,000 per month depending on which components they purchased.

By the time of this interview, Sunroof had signed three customers, each paying around $4,000/month at the minimum tier, translating to $12,000 MRR. For a bootstrapped company barely a year old, landing enterprise banking customers was significant validation.

The biggest challenge at this stage wasn't sales—it was customer success. With only three customers and a lean team, Travis hadn't yet built dedicated customer success managers. He recognized this was limiting feedback and product decisions: "We're not collecting enough feedback from our customers to make the true blue product decisions we need to be making."

This realization pushed him toward raising capital. Despite being profitable at $12k MRR, he saw the market opportunity as too large to attack alone. "The market's just sitting there for the taking," he said. A safe note allowed him to bring in team members (especially dedicated customer success managers) and sales capacity without the distraction and dilution of a traditional equity round.

Travis was raising $1 million on an $8 million cap via a safe note with standard 20% discount and 8% interest rate. His goal was to scale from 3 customers to 50 within 12 months and then move into Series A fundraising. He was deliberate about alignment: common shares across the cap table meant all stakeholders (including investors) shared the same upside, with no preferred stock creating misaligned incentives.

At 37, single with no kids, Travis was fully committed to building this one right. He'd learned from his first company that chasing high valuations early sets unrealistic expectations and sets you on a treadmill of endless capital raises. This time, he wanted to build "very strong, healthy software businesses" that could eventually reach the $10–50 million ARR range without perpetual fundraising. The early traction in the fragmented lending market suggested he might have found a better long-term fit.