HiRISE

Nathan Contney's entrepreneurial journey began with frustration at large corporations. Working at Accenture early in his career, he observed that decision-makers ignored insights from employees and broader communities. "I felt like a lot of us as employees had a lot of great ideas and input and insight in how things were going, but nobody's paying any attention," he recalls. This observation sparked the idea for Inkling in 2005—a prediction market platform that would democratize decision-making by letting employees and stakeholders place virtual bets on project outcomes. The concept attracted Y Combinator's attention and eventually major clients like Procter & Gamble and the U.S. government. But after six years building Inkling, Contney felt trapped. The company's success came from serving massive organizations with complex needs—the opposite of his original vision. He couldn't use his own product, couldn't trust his instincts, and spent his time in meetings with corporate clients rather than designing. "I couldn't use my instincts anymore. It was always like, well, we better have a meeting with the folks at Procter & Gamble to see what they need," he explains. He decided to pursue a different philosophy: build products for problems he experienced himself.

After leaving Inkling in 2011, Contney co-founded CitiPosh with his former Inkling partner, also through Y Combinator. The idea borrowed from the success of Zynga and Groupon—a gaming platform where brands could embed their logos into addictive games like Bejeweled. Players would engage with brand imagery constantly, theoretically driving purchase intent without explicit advertising. The team achieved impressive engagement metrics: two hours per day per player, matching Zynga-level numbers. But they made the same mistake twice. "We basically created something to help companies like Procter & Gamble and people advertise on the internet better," Contney admits. The product still wasn't for him. When it came time to sell to brands, the team faced brutal sales conversations about ROI on advertising spend—a metric they couldn't easily prove. Exhausted from six years of similar challenges at Inkling and lacking passion for the vision, Contney and his partner gave up. He took a break, spending six months working on the Obama campaign's tech team in 2012—which he found "more relaxing than running a startup."

Contney's breakthrough came from scratching his own itch. He'd been building an audience through consistent writing on a personal blog, publishing one article weekly starting around 2011. He identified real pain points in his own workflow: version control for documents, collaborative editing without losing control, and difficulty managing multiple drafts with editors. In 2013, he launched Draft as a solo founder, initially funded by leftover capital from CitiPosh. Rather than chase customers, he built the product he desperately needed and relied on his existing audience to discover it. His writing habit—maintaining a cadence of one published piece per week—created a natural channel to share updates about Draft. The blog became his marketing engine, and his credibility as a prolific writer made Draft's value proposition obvious to fellow writers. He used a simple freemium model: free to use until you hit a document limit, then a nag screen asking for $4/month. Though minimal, this was enough to cover costs and validate that people would pay for better writing tools.

Contney's greatest innovation as a solo founder wasn't product features—it was imposing discipline through cycles. He committed to shipping three features every three weeks, announced via a customer newsletter. "That forced me into a way to prioritize things," he explains. When the deadline loomed, he'd abandon perfectionistic polish and ship whatever was ready. This created momentum, which became his singular priority. Everything else—including customer support—took a backseat. "If you want to optimize for it, go for it. But it couldn't have been my top priority because you can only have one priority." He outsourced ruthlessly: Heroku for infrastructure, Indie Nero for accounting, Lead Genius for editing services. This freed him to focus on product and marketing. Draft succeeded because it solved his problems better than competitors. "I could point to no one is doing version control as well as draft does version control," he notes, referencing features like accepting individual suggested changes rather than all-or-nothing edits. The lesson: start with deep personal knowledge of a problem space, not broad customer research. "Most people should start there. What problems do you face yourself? Start working on those before and run that well dry before you start trying to take on other people's problems."

Draft continues operating as a sustainable but small business, generating enough monthly recurring revenue to fund one full-time or part-time developer—though Contney hasn't hired anyone since taking over as CEO of HiRISE, the CRM platform originally built by Basecamp. He still uses Draft daily for his own writing and keeps it maintained for existing customers. The product never exploded in scale, partly because he stopped prioritizing it once HiRISE demanded his attention. Yet its elegant simplicity—stripped down to essentials by necessity—earned devoted users who appreciate what Contney calls "peeling back the layers" to discover hidden capabilities. Contney met Jason Fried of Basecamp through the startup community and was eventually offered the CEO role at HiRISE. Now managing a full team, he faces different challenges: scaling a product beyond solo-founder constraints, managing customer expectations, and building organizational infrastructure. The psychology of startup leadership remains his focus. "Even in High Rise, I mean, we still make a bunch of mistakes and we still get frustrated and we still want certain things to be working out better," he says. His philosophy remains unchanged: "Done is better than perfect." The difference now is executing that principle at scale rather than as a solo founder shipping features in three-week sprints.