Bridge Venture Fund, Upfront, Lumber: The Sure Shot Entrepreneur Newsletter

Hello Reader,

Founders are strong believers in the ideas they bring to life. The early investors are strong believers too. Paradoxically, the very same people have to remain skeptical and test the underlying viability throughout the lifetime of the startup. It requires a strong focus on the value proposition and customer pain points to identify the true signal of startup success. This allows founders and their investors to actively navigate (/pivot) to safer ground than running headlong into the rocks behind frothy waves.

Connor Ryan, my podcast guest this week, said, “There’s infinite product-market fit for giving away a dollar in exchange for 99 cents.” He does not look at the sizzle of traction and pipelines. He looks deeper beyond the standard metrics into actual unit economics to get convinced and make investment decisions.

Mark Suster, my guest in episode #83, had similar sentiments. He looks at the track record of the company for tangible evidence of product market fit.

– Gopi Rangan, Host of the The Sure Shot Entrepreneur podcast

Startup Corner: Lumber

Lumber, an AI-powered construction workforce management platform, has joined the Fulfilled by Acumatica program, ensuring seamless integration with Acumatica’s cloud ERP platform. This collaboration streamlines payroll, compliance, and HR processes, enabling construction businesses to improve efficiency and track real-time labor costs.

Lumber’s innovative approach helps companies navigate prevailing wage compliance, union agreements, and workforce management challenges while delivering AI-driven insights for smarter decision-making.

"Joining the Acumatica Marketplace is a milestone for Lumber," said Shreesha Ramdas, Founder and CEO of Lumber. "This partnership ensures our users maximize their Acumatica ERP investment while enhancing workforce management capabilities."

Show Real Traction, Not Just Projections

My guest in Episode #160 is Connor Ryan, Partner at Bridge Venture Fund. Connor shares his journey from investment banking and private equity to venture capital, where he focuses on investing in overlooked sectors underserved by innovation.

Connor emphasizes the importance of identifying companies that demonstrate sustainable unit economics rather than relying on forecasts alone. He discusses Bridge Venture Fund’s approach to backing startups that bring meaningful efficiencies to industries like legal tech, construction, and frontline workforce management.

We also explore why he values understanding a product’s real-world user impact and how he evaluates founders based on their ability to articulate customer pain points and demonstrate tangible results.

Listen to the episode

Connected Insights:

Evaluating Founders: From Trendlines to Tangible Proof

In episode #83, my guest was Mark Suster from partner at Upfront Ventures. Mark emphasized that venture investing is about tracking a founder’s progress over time—connecting the dots to form a trajectory of performance. In the episode, he highlights how he looks for tangible evidence of product-market fit rather than projected success, stressing that execution, founder reliability, and real-world proof matter more than high-level pitches. His investment decisions are based on demonstrated progress and measurable traction.

Community Involvement:

World Wildlife Fund

Connor Ryan is passionate about the World Wildlife Fund (WWF) and its mission to protect wildlife and restore biodiversity. He believes conservation plays a vital role in mitigating climate change, as biodiversity loss has accelerated dramatically, with global wildlife populations declining by 70% since 1970.

WWF works globally to protect endangered species, restore habitats, and advocate for policies that promote ecological balance. By preserving natural ecosystems, WWF helps combat environmental degradation and ensures long-term sustainability.

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