Latergram

Matt Smith was co-founder and CTO of Thinkific, an online course platform he built with his brother that had reached $10K MRR by November 2014. While running Thinkific, Matt attended a hackathon in November 2013 with friends, including co-founder Ian McKinnon. During brainstorming, McKinnon suggested an idea that immediately excited Matt: a tool to schedule posts to Instagram. Matt's inspiration came directly from a friend who was struggling to manage a large retail brand's Instagram account (similar to Forever 21), coordinating posts across the country via text messages with team members. "When he mentioned the Latergram idea of sort of figuring out a way to schedule posts to Instagram, I kind of jumped at it and was really excited."

After the hackathon in November 2013, Matt and his co-founders spent six months building Latergram while maintaining other commitments. The product was relatively simple but solved a real problem: Instagram's native app didn't allow scheduling. Matt was working nights and weekends—"literally building the company in our pajamas and bedtime, like, you know, I just sit there and basically fall asleep, getting the last few hours and, you know, punching and, you know, doing a little coding or like emailing people." By May 2014, they launched publicly without a traditional beta phase, instead slowly accepting signups. The lean approach paid off: by launch month, they had accumulated 20,000 signups.

The path to those 20,000 early signups wasn't accidental. Matt executed a multi-pronged founder-driven acquisition strategy. First, he created a "VIP program" (which he admits was more marketing positioning than actual program) and personally emailed nearly all 20,000 early signups, spending most evenings writing personalized messages. "I think when people see, you know, a founder doing that, they say, and they like the product and like what they're going to offer, I think they're more than willing to write about it." The effort worked because the target audience—bloggers and social media managers—were themselves skilled at building audiences. They understood the product's value and voluntarily wrote about it. Matt says many people came to him asking to write articles rather than the other way around: "I never asked really, that was the thing was great because I was just really caring about our users and the customers and who they are."

Timing also mattered. When Latergram launched, there were only hacky solutions for Instagram scheduling—no polished, purpose-built platform. "When we came in and did that and offer that and did a nice, there was aesthetically pleasing UI was easy to use. I think people just jumped on the opportunity to share that and talk about it."

By early 2016, Latergram had scaled to nearly 500,000 users (both free and paid), with approximately 3,000-4,000 paying customers generating $50,000 MRR. The freemium model was intentional—Matt's goal wasn't to maximize near-term revenue but to maximize growth and engagement. With a typical 5% free-to-paid conversion, they focused on usage metrics: 40,000 monthly active users (defined as posting at least one image per month via Latergram). Customer retention was healthy at 95% monthly retention (5% churn), though some "churn" was actually customers moving between free and paid tiers or using the product seasonally.

Their growth channels remained entirely organic: SEO (they ranked well for relevant search terms), content marketing (still building this out), ambassador and word-of-mouth programs, and email marketing (newly ramped up). They deliberately avoided paid acquisition—"we might in the future, but at the current point, we're really kind of nailing our organic acquisition channels that have worked really, really well."

In May 2014, just weeks after launch, a VC firm called Rocket Ship (founded by early Facebook employees) cold-emailed the team and offered to invest. Matt was skeptical initially—"we had really nothing more than an app in the app store and a web based product and a few thousand users." But Rocket Ship believed in the growth trajectory and invested $1.2M via a SAFE note. The capital gave the team confidence to fully commit to Latergram (Matt had left Thinkific as CTO in January 2015 to focus entirely on it). The team quickly expanded to 11 employees, all based in Vancouver—a strategic choice due to lower salaries (offset by government grants covering up to 80% of tech salaries) compared to Silicon Valley.

With the seed closed and additional angel investments from Heaton Shaw and Aspect Ventures, Latergram aimed for ambitious 2016 targets: 25-30% month-over-month growth with a goal to reach $1M ARR (roughly $88K MRR). Matt preferred to think in terms of trajectory rather than fixed revenue targets, focusing on compounding monthly growth. At 31 years old, Matt reflected on the journey: "You don't need a job." His path from building Thinkific to pivoting to Latergram, while unconventional, proved that great product-market fit and founder hustle could move faster than institutional processes.