Most people at the Smart Marketer Mentor Table have a clean origin story. Rob Schmidt’s is not one of those stories.
By 32, Rob had co-founded two telemedicine brands, Winona (prescription HRT for women in perimenopause) and Willow (prescription GLP-1s for weight loss), and was running over $8 million a month in paid media across both. He’d also, at various points before that, worked as the CFO of what would become ClickUp, burned through his savings, racked up credit card debt, lost his father, and moved into a trailer with his mom.
The path from there to $300 million in projected annual revenue is not a straight line. But if you sit with Rob long enough, which we did at this year’s Mentor Table, the principles underneath that trajectory start to come into focus.
Here’s what stood out.
The six months in a room that changed everything
After ClickUp was relocating to San Francisco and Rob didn’t want to follow, he left the company and took what he describes as a six-month hiatus. By his own account, he hadn’t fully processed his dad’s death, his sister had nearly died, and most of his money had gone toward taking care of his family.
So he locked himself in a room. Read everything he could find. Took every digital marketing course available, including Digital Marketer, which he tracked down by intentionally following marketing influencers online just to get retargeted. He says he just kind of finalized his education there. That led to a marketing consultancy, which led to a client in solar, which led to a venture studio, which eventually led to Winona and Willow.
The point isn’t that isolation is a strategy. The point is that the low point became the foundation. He used the time to actually learn the craft, not just talk about it.
What changes when you’re spending $300K a day
Most brands learn paid media by doing paid media. The challenge is that the mental models that work at $1,000/day don’t always transfer cleanly to $10,000/day, and definitely not to $100,000/day.
One of the biggest shifts Rob described is how you think about attribution. At lower spend levels, picking one attribution model and sticking with it is usually fine. At scale, it starts to break down. He’s seen it firsthand: certain ads perform better on certain attribution models and worse on others, and if you’re only looking at one model, you’ll make cuts you shouldn’t make.
His fix: stop looking at attribution models in isolation and start indexing them side by side. Seven-day, 30-day, last-click, first-click, linear, all of it, in one view. His team built a custom internal marketing science platform to do this, but he’s quick to point out that most brands don’t need to go that far. Even pulling your data into Airtable and comparing multiple models in a simple table is a massive upgrade over picking one window and trusting it blindly.
The tool they landed on after testing most of the major players? Hyros, mostly because it exports clean click-level data, which is what they actually care about. Triple Whale, he noted, does a good job filtering bot clicks, so there’s that.
The click-level data most brands are ignoring
Here’s the thing about third-party attribution platforms: most of them are a black box. They’ll give you a number, but they won’t give you the underlying click data that produced it.
Rob’s obsession with click-level data comes from a simple insight. When you have the raw clicks, you can start answering questions that platform dashboards can’t. How is organic actually converting? What role is email playing in a conversion path that started with a paid ad? What are affiliates actually contributing? You can splice the data differently depending on what you’re trying to understand.
His first recommendation for anyone who wants to move in this direction: just get the referrer data. If someone hits your site from Google without any UTM parameters, that’s an organic visit. Where they land tells you something about what brought them. It’s not perfect, but it’s a starting point for actually measuring the thing everyone says they want to measure.
The more sophisticated version, fingerprinting anonymous IDs, building customer profiles from first-party data, doing your own media mix modeling, comes later. But the referrer variable is free and available right now.
Brand vs. direct response: an honest take
This is one of those debates that can eat a lot of meeting time without producing much. Rob’s view is pretty direct: he always prioritizes direct response, because the brand won’t exist if you don’t get customers first.
He’s not anti-brand. For Winona and Willow, brand has real authority, specifically over anything that gets indexed on their site. Their medical journal, their blog, anything SEO-facing. That’s brand’s domain.
But for ads, they removed brand from the review pipeline entirely. His take is that brand teams can get overly precious, and the reality is you never know your customer as well as you think you do. The vernacular they use, the things that resonate with them, the way they actually talk about their own problems. If your message is landing well enough that people want to buy, you’re doing the job.
His framework: if it lives on your site and gets indexed, brand should have weight. If it’s a paid ad, let the market decide what resonates.
The leadership thing nobody talks about
When asked how he’s had to grow as a person to lead companies at this scale, Rob didn’t reach for a quote about vision or culture. He went straight to delegation.
Most people running fast-growing companies are control freaks by nature, he said, and learning to be okay with outputs from other people that aren’t exactly to your standards but are good enough to move things forward is one of the hardest real skills in the job.
He also made a point about staying humble enough to revisit fundamentals. Even things you learned years ago. Even talks where you already know everything being presented. Being open to hearing it again is what lets you actually receive the information and remember what you’ve forgotten.
It’s easy to dismiss that as generic wisdom. But coming from someone running eight figures a month in ad spend who voluntarily shows up to events like this one, it lands differently.
What’s next: a house of brands at scale
Rob’s near-term roadmap is ambitious. He’s launching an internal platform that will let his team spin up new brands significantly faster than before, and with AI in the mix, he sees a clear path to a multi-billion dollar house of brands within three years.
Winona is expanding into in-person med spas and clinics. Willow is moving into physical kiosks. And the venture studio that predates all of this is still kicking out companies, including a hard-sided pop-up camper brand he describes as a real pain in the ass.
He also plans to retire from traditional work at 35. His post-retirement plans include getting involved in foster care, exploring politics, and, seriously, becoming a professional treasure hunter. That plan involves visiting universities around the world, interviewing historians about things people believe might be real but probably aren’t, and then just going to look for them.
He wants to hire Nicholas Cage to come along on at least one expedition. He means this genuinely.
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