Aaron Hoffman started his delivery company at 19 years old from a college dorm room. He wasn’t trying to build a tech empire — he was just cold and didn’t want to walk to the dining hall.
That very human moment became Deliver That, a company that now does $25–30M in annual revenue, serves national restaurant brands, and operates one of the only independent delivery management platforms in the country. Twelve years, zero venture funding, and a 2.2 GPA.
In Episode 4 of the HappyFleet podcast, Aaron joined host Robert Fierro for a conversation that covered the full arc — from dispatching deliveries while at the bar with his fraternity brothers, to building software that he believes can help restaurants take back control of their own customer experience.
The Origin Story
Aaron was a pre-med student at a small Ohio college when, one cold day, he thought: I’d pay someone to do this for me. He made a Twitter account, went viral on campus in three days, and had five to six people shuffling through his dorm room with cash envelopes.
His co-founder is his best friend from elementary school. Twelve years later, they’re still partners — in part, Aaron believes, because they never lived together. Business and friendship occupied separate lanes.
The company pivoted twice: first from campus delivery to professional catering delivery for restaurants, then again post-COVID into tech-enabled delivery management software. That last pivot was born from frustration — there was nothing on the market built specifically for the catering delivery use case.
“There’s nothing that’s really focused on food delivery or large order delivery,” Aaron says.
So he built it himself. He spent six months learning software development from scratch, watching tutorials four to five hours a day, then convinced one of the smartest people he’d ever met — now his CTO — to bring his vision to life.
Book a demo and start your free trial today →
Bootstrapped by Choice
Twelve years in, Deliver That has never taken outside funding. Not because investors weren’t interested — Aaron describes himself as probably the worst fundraiser you’d ever talk to — but because the business never needed it.
“We’ve been profitably growing,” he says. “We run this business with a certain philosophy, and that’s not to operate like you have a blank check.”
It’s a mindset forged in the Midwest, where hard work and resource discipline aren’t just values but survival instincts. While venture-backed competitors were burning cash, Aaron was grinding his way to a business that could sustain itself.
The Tech Pivot and Why It Mattered
When Aaron stepped back as CEO in late 2021 to focus on building software, the core insight was clear: technology built for general delivery wasn’t solving the specific, time-compressed chaos of catering.
“Catering is a very cyclical business,” he explains. “Most of the volume hits between 10 and 1 on weekdays.”
That window demands precision — more drivers than you can reliably staff, all dispatched at once, to high-stakes corporate clients.
The software Deliver That built — delivery orchestration, a driver app, automated routing — didn’t just improve efficiency. It changed how they could grow. Pre-software, launching a new market meant flying to Phoenix for six weeks, doing ride-alongs, building relationships with local drivers, and hoping things held together when you left. Post-COVID, post-software, they could recruit, equip, and get drivers on the road in three to five days without anyone physically on the ground.
Today, a last-quarter all-hands milestone stood out: for the first time ever, zero percent of deliveries were routed by humans.
What $30M in Revenue Didn’t Buy Him
Here’s the part of the conversation that cuts deeper than the business metrics. At the moment Aaron was making the most money he’d ever made, he was also the most unhappy he’d ever been.
“I thought money would give you freedom. It has done that, but I didn’t get that sense of fulfillment.”
He draws a parallel to Rory McIlroy winning the Masters — completing the career Grand Slam, achieving what he’d worked his whole life for — and still feeling the same. “I want to go one more.”
For Aaron, the shift happened in 2024. The goal stopped being revenue and started being impact.
“I really want to create something novel that makes an impact in humanity in some capacity.”
He wants to be known not for the dollars but for the dent.
What actually brings him joy? Watching a restaurant save over a million dollars in six months by sidestepping marketplace fees. Seeing a tech company license Deliver That’s driver app and grow their own business with it.
Book a demo and start your free trial today →
The Four Business Lines and Where It’s Going
Today, Deliver That operates across four solutions: a 50,000+ gig worker delivery network, delivery orchestration software, a self-delivery app for restaurants and tech companies, and Gig Supply Plus — equipment, packaging, and supplies for drivers and DSPs.
Two more launches are coming: a driver placement product — essentially driver recruiting software for companies that need pre-vetted, delivery-experienced hires on demand — and an intelligence platform built around a key differentiator. Deliver That is the only national delivery company not financially tied to a third-party marketplace. That independence means they can actually tell restaurant brands what’s best for them — not what’s best for the platform.
On autonomous delivery: Aaron is watching closely. He sees drones and bots as natural next steps for certain delivery types. But a $1,000 catering order going to the 50th floor of a Cleveland office tower? Still a human job, at least for now.
The Long View
Aaron is 32. He graduated with a 2.2 GPA. He was running a functional business in college while his entrepreneurship professor admitted to never having run one. He’s building a company he hopes will change something real about how the restaurant industry operates.
His advice for anyone in business, borrowed from a conversation he keeps having about AI:
“Get curious. See what it can do. Try to learn a little bit.”
The calculator didn’t replace math — it just changed what mathematicians could accomplish.
Same story, different decade.
This post is based on Episode 4 of the HappyFleet podcast. Connect with Aaron Hoffman on LinkedIn or learn more about Deliver That at deliverthat.com.
#AmazonDSP #LastMileDelivery #DSPHiring #HRTech #AIRecruiter #DSPOwner