He's mid-pitch before you realize the pitch already worked. David Siteman Garland - DSG to everyone who has bought a course, heard a webinar, or stumbled across The Rise to the Top on a Sunday morning in 2009 - figured out the online course business before Teachable, Kajabi, or any of the platforms that now claim to have invented it.
The origin is genuinely strange. In 2008, a recent Washington University graduate - Women's Studies major, former inline hockey goalie, Bar Mitzvah money still in a savings account - cold-pitched a St. Louis TV station and bought airtime on ABC. Not to sell ads. To host a show. He called it The Rise to the Top, interviewed local entrepreneurs, and ran it for two seasons before deciding local was too small a word.
The pivot to the internet was less a strategy than an impulse. He switched to Skype. His first online guest was Peter Shankman. Within a year he had Seth Godin, Tim Ferriss, Gary Vaynerchuk, Tony Hsieh, Daymond John, and Barbara Corcoran on tape. He grew an email list past 100,000 subscribers. He got a book deal with Wiley - "Smarter, Faster, Cheaper," published 2010. The New York Times covered it. The Wall Street Journal covered it.
None of that is the thing he's proudest of.
In 2011, DSG launched a $495 online course called Create Awesome Interviews. The first week: $19,800. By month twelve: $250,000. He realized he had stumbled into the actual business model. By 2013, podcast sponsorships were pulling in $150,000 a year - including a $100,000 deal with Citrix sitting in his inbox. He turned it down. On December 31st, he announced the podcast was done. He went all-in on courses.
The first launch of Create Awesome Online Courses: $275,000 in five days. He learned a new webinar structure from an Irish entrepreneur named John Richardson the night before a scheduled event and watched his per-event revenue jump from $8,000-$9,000 to $38,000 - then $111,000-$118,000. Then $311,000 in a single five-day window. A single partner webinar with John Lee Dumas of Entrepreneur on Fire: $220,000-$230,000 in one session. Cumulative sales eventually crossed $10 million. The team headcount: four. One of them is his father, VP of Customer Service.
"Money follows passion and not the other way around."
- David Siteman Garland
The business runs at margins most software companies would envy. DSG works from home in the Central West End neighborhood of St. Louis, takes midday workout breaks, coaches his kids' basketball teams, and describes his wife Dr. Marcie Garland on his own website bio as "way smarter than him." It reads like a joke. It probably isn't.
The family context matters. DSG is the grandson of Alvin J. Siteman, the St. Louis businessman whose $35 million gift created the Alvin J. Siteman Cancer Center at Barnes-Jewish Hospital and Washington University School of Medicine - one of the nation's leading cancer research institutions. His grandmother, Ruth Levinsohn Siteman, passed in June 2024 at 92. DSG grew up watching what it looks like to build something that outlasts you. Then he built his own version: 5,000+ students in 100+ countries, many of whom have since built their own course businesses from scratch.
One student, Rene Christine - divorced single mother - made her first $3,000 in course sales in 2015 after enrolling in Create Awesome Online Courses. By 2017, she had crossed $1.7 million. DSG will cite that number faster than he cites his own revenue. The framing is deliberate: he measures the business by the wins it creates downstream.
Beyond courses, DSG has built a small portfolio of software companies. Course Cats was a WordPress theme for building course websites without designers. Conversion Cats followed as a personal brand website platform. That became Nrdly - a bootstrapped website platform for authors and content creators with a complimentary concierge setup service. He co-founded LeafBridge for e-commerce infrastructure in the cannabis space. Siteman Garland Enterprises operates as the private equity arm.
In fall 2024, he founded STL Maccabi Basketball - St. Louis's first competitive Jewish youth basketball program - starting with 8 second-grade boys. By 2025, it had expanded to two teams and 16 players. That is either a hobby or the next thing. With DSG, those two categories have historically been the same.
He is not a guru who talks about building audiences while quietly never building one. The email list has 85,000+ real subscribers. He personally answered every comment in the early years. The brand voice - non-boring, anti-fluff, no buzzword nonsense - holds across a decade and a half of content because it was always just how he talks.
The origin story closes the loop: a Women's Studies graduate with Bar Mitzvah savings, a borrowed Skype connection, and a willingness to drop $100,000 on the table and bet on the thing nobody else was calling a real business yet. He was right about the internet interviews before podcasting existed. He was right about online courses before the platforms existed. The Rise to the Top turned out to be the most accurate brand name he could have chosen - even if the title was written before he knew what it would take to climb.
