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Pitch, Run, and Scale - Launching Upscale AI
How Pitch and Run helped Upscale get funded, find customers and Launch
Dorothy Chau, Kat O’Brien & Kevin Weatherman
May 21, 2025
Some communities change your trajectory. For us at Upscale AI, Pitch and Run wasn’t just a support system—it was a catalyst that helped us scale from idea to launch.
In March 2024, I shared with Nihal Mehta—co-founder at Eniac Ventures and one of the driving forces behind Pitch and Run—that I was leaving my job to cofound a new company. My cofounder? Former Eniac portfolio CEO Herman Yang, an experienced Eniac portfolio founder whose background at the intersection of programmatic advertising and AI made him the ideal partner to pursue a major opportunity: turning streaming TV into a true performance channel for eCommerce brands.
We had a big vision: use generative AI and machine learning to make TV ads measurable, scalable, and creative at startup speed. What we didn’t have—yet—was product-market fit, early adopters, or even working creative. Check us out https://www.upscale.ai/how-it-works
Pitching Upscale at the Eniac offices after a run
Upscale AI founding team at our first offsite in the Enaic offices in NYC
“This story is another reminder of how life is long—especially in venture. I first met Kevin Weatherman back in 2011 when he was early at MoPub and I was running my startup LocalResponse. Kevin and I became friends and we co-invested in many companies together (including Attentive and Ghost) and we eventually co-founded Pitch and Run together in 2019. Independently, in 2016, Eniac Ventures met and led the seed round for Herman Yang's martech startup, Chatgrid.
So when we heard last year that Kevin, Herman, along with co-founders Mike Chang and Seth Yates, were teaming up to leverage generative AI to disrupt creative budgets and help marketers seamlessly create and stream TV ads, we jumped at the chance to lead their pre-seed. Right team, right time.
Source: Nihal Linkedin Post Header - Pre Seed Closing Dinner
The First Customer? Another Pitch and Run Member
Before we had a product, we needed a partner willing to give us a shot. That first believer was Kyle Bergman, founder of Swoveralls and a fellow Pitch and Runner. He didn’t just encourage the idea—he became our first design partner. That early feedback cycle helped us iterate fast, validate our creative generation engine, and build something real.
Meeting with Kyle in NYC before we launched our first Ad
Tapping into the Shopify DTC Community
Another major unlock came through engaging with the broader Shopify DTC ecosystem—specifically via Founders Only, the community started by Chaitenya Razdan, who also organizes the Thursday morning Battery Park Pitch and Run. Through Chaitenya’s events, we connected with dozens of breakout DTC brands, including The Perfect Jean and Splendid Spoon.
One highlight? Winning a Jolie Showerhead at a Founders Only casino night—an unexpected reminder of how serendipity and community go hand-in-hand. These connections, built at galas and pickleball courts, accelerate introductions, learnings, and trust across the ecosystem. It’s another reason why we believe building a brand doesn’t just happen in your office—it happens wherever the best founders hang out.
Finding Talent in the Network
As we began stress-testing early creative tools, we needed video editors to experiment with. Where’d we turn? Pitch and Run. Several early editors came through the group—people who were generous with their time and eager to explore the overlap of creativity and AI.
Then came another huge unlock: Brandon Blum. We met Brandon through Pitch and Run, and his story is one of the best examples of what makes this community special:
“In early 2024, I was at lunch with my friend Dustin Kendrick, a P&R regular, when he suggested I join him at Pitch & Run. That first run down the west side highway opened doors I didn’t even know existed. P&R became part of my weekly routine, and even when I moved outside the city last summer, I stayed connected through the WhatsApp group. When I saw Kevin post about ‘Founders Basketball’ in late 2024, I signed up immediately and eventually convinced him to let me take the reins on the event. This led to Kevin and me working together more consistently, and when Upscale.ai needed someone to run and grow their social media, the connection was already there. I’ve been their fractional head of content ever since — all thanks to the power of the P&R community. Need an extra hand with your business’ content? Shoot me an email and let’s chat ([email protected])”
Dec Founder’s Basketball
From Runs to Raise
That first conversation with Nihal wasn’t just a friendly update—it was a spark. Eniac led the pre seed round along with Breakpoint Capital, and SuperAngel.Fund. Then, 6 months later nvp capital led the Seed and Eniacn once again helped by introducing us to M12 (Microsoft’s fund). Combined we raised $5.5M in funding to build a platform that could reshape how eCommerce brands win on the biggest screen in the home .
The Outcome
As of May 2025, we’ve launched Upscale Studio—an AI-native platform that helps eCommerce brands generate high-quality streaming ads, run them through machine learning-optimized media buys, and measure outcomes with precision. We’re live with brands like Branch, Lalo, and yes—Swoveralls.
But it all started with a few morning runs.
Pitch and Run didn’t just give us endorphins and a sense of community—it gave us our cofounder, our first customer, early team members, and the courage to build. Btw we’re hiring https://www.upscale.ai/careers
If you’re building something ambitious, surround yourself with people who move fast and sweat together. It worked for us.
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