Seen and Heard at TechChicago Week 2025: Founder Advice, Fundraising Tactics, and a Little Soccer

TechChicago Week 2025 was packed: panels, pitches, rooftop parties, and a lot of valuable knowledge being shared. A few things stuck: early-stage operators in Chicago need to focus, fundraising is more competitive than ever, and thoughtful follow-up can win deals. We caught sharp insights from founders and operators like Ryan Fukushima and Ben Weiss, got real talk on VC process from Haley Bryant and Vignesh Ravikumar, and saw Chicago:Blend’s community share their points of view on topics from gaming to the similarities between shutting a company down and losing a pet. Plus, we kicked things off the right way: with soccer, drinks with a skyline view, and some friendly competition.

Here’s what we saw and heard at TechChicago Week 2025.

Operating Early: Build, Sell, and Focus

Ryan Fukushima (TempusAI)

Ryan Moved to Chicago post-MBA and mapped out the top people he wanted to meet in startups, leading him to Techstars Chicago. His strategy: add value, even if it meant working for free. It worked and those early bets turned into roles at Hyde Park Venture Partners, Lightbank, and eventually the early team at TempusAI after forging a close working relationship with Eric Lefkofsky. His advice for founders:

• “Put yourself in a position to be lucky.”
• Be skeptical of belief. Don’t commit until a customer proves it with money.
• Early-stage? Forget strategy. Your only job is building product or selling product. If you’re not focused on those two things, you aren’t moving forward.

Ben Weiss (CoinFlip)

When Ben was asked by an early-stage founder how it’s possible to remain competitive against much better-funded incumbents, he encouraged them to go niche,“Big players like Amazon can’t go niche. Every time I’ve gone broad, it’s created problems.”

That same discipline applies beyond product. In the early days, niche positioning sharpens everything: your customer targeting, your messaging, your GTM strategy, even who you hire. Trying to be everything to everyone slows execution. Narrow the scope, move faster, and succeed a slice of the market before expanding.

Fundraising: Competition, Process, and Founder Memos

Haley Bryant (Hustle Fund)

Haley pulled back the curtain on how early-stage VCs actually evaluate deals and emphasized that your startup isn’t judged in a vacuum. “We’re stack-ranking across deals. Traction matters, especially in the first 0–6 months.” Out of 15,000 applications in the last twelve months, Hustle Fund saw more founders than ever with real sales and product progress early on. She also hammered in on the power of consistent follow-up, noting she’s backed founders because their updates showed clear momentum and execution.

Vignesh Ravikumar (Sierra Ventures)

Vignesh shared straightforward fundraising advice in the current environment:

• You need 12 months of runway going into a raise, “If you’re at 6 months, you’re not raising from a position of strength.”
• “Don’t chase dead leaves.” - VCs who feign interest but won’t commit or those that decline you even if you think they are a great fit. Move on - you’re not trying to get 20 yeses, you’re trying to get one.
• He loves founder memos being shared by teams during the investment process because they:
  
  • Clarify founder thinking
  • Make internal VC workflow easier
  • Surface insights missed in pitch meetings and allow founders some control of their narrative

Chicago:Blend Talks

Chicago:Blend brought their well-loved Blend:Talks to the Capital Summit this year. Some highlights from the presentations:

• Gail Wilkinson, Managing Partner of VITALIZE VC, on startup shutdowns as she sunsets her own fund: it’s similar to the grief of losing a pet. Vulnerability during the process will open up doors, help you find kindred spirits, and may put you on to your next idea.
• Grisel Hernandez, Senior Associate at Chingona Ventures, described modern work as a “hyperactive hivemind,” where our brains are overloaded trying to track tasks, meetings, and messages. Her take? The future of AI isn’t about replacing jobs, it’s about coordination. AI could free up mental space by managing the chaos - filtering noise, automating follow-ups, and helping us focus on actual thinking instead of just keeping up. In short, “The brain is for having ideas, not holding them.”
• Mijin Han, Principal at Korea Investment Partners, highlighted that gaming has hit $220B globally, making it larger than the film and music industries combined. It’s not just entertainment—it’s culture, commerce, and community. Gamers span every demographic, and platforms like Roblox, Fortnite, and Twitch are blurring the lines between gaming, social media, and live events. For founders, it’s a massive, underleveraged market with room for innovation in creator tools, virtual economies, and AI-driven experiences. Ignore it at your own risk.

TechChicago Week KICKoff with LongJump, Chicago:Blend, LaFamilia, and VamosVentures

We brought back our popular rooftop soccer happy hour to get the week started with some friendly competition. Founders faced off against VCs and ecosystems partners in a mini-tourney that saw Gabriel Huertas del Pino (Founder, Arch Pet Food), Craig Silver (Founder, Sous), Shawn Park (VC, Chicago Ventures), Casey Lawlor (Founder, Unvale) and Felipe Platzor (Founder) walk away with the TechChicago Cup!

Many thanks to J.P. Morgan's Innovation Economy team and CDW for sponsoring! Did we catch you in action at the KICKoff? Check out the pictures below ⬇️