How to hone your startup pitch for every audience — and avoid ‘show-up-and-throw-up'
At the 'Honing Your Pitch: For Sales, Investors & Employees' panel at the 2025 Technical.ly Builders Conference, three seasoned leaders shared what makes a pitch resonate and what many founders still miss.
Moderated by Barry Wright, an executive at healthtech company Noom, the panel featured Ben Bartolome, vice president of commercial banking for startups at J.P. Morgan; Naza Shelley, founder and CEO of matchmaking startup CarpeDM; and David Cummings, founder and CEO of Atlanta Ventures.
'You'll pitch about 10,000 times in the life of your startup,' Wright said. 'Every conversation is a pitch.'
One takeaway from panelists is to be deeply prepared, but share just enough to spark interest without overwhelming your audience.
Shelley, whose startup has raised more than $2 million, said preparation is crucial, especially for underrepresented founders.
'Asking for money is hard and harder for minorities, and triply so for Black women,' Shelly said. 'If I don't know an answer cold, I'm written off as incompetent. I learned I must be super prepared, know every detail, anticipate every question.'
Cummings, a co-founder of marketing automation company Pardot and early Calendly backer, offered a hard-won lesson from his early years as a founder.
'I suffered early from the 'show-up-and-throw-up,'' Cummings said. 'I wanted them to know every detail and got lost in word salad. Now, I simplify. Give just enough, with a hook, so they say, 'Tell me more.' If I overwhelm them, I fail.'
Even when a pitch doesn't go as planned, there's often lessons to take away.
Bartolome, a former fintech founder, recalled a fumbled B2B negotiation that cost him a six-figure deal and valuable traction.
'They wanted 5% equity for early partnership,' he said. 'I refused. We haggled over single-digit points and lost a six-figure [annual recurring revenue] deal plus strategic momentum. In hindsight, that 5% was nothing compared with the benefit.'
How to handle the talkative investor
What do you do when a potential funder won't let you speak?
'Be excited,' Shelley advised. 'They're engaged. Flow with their questions, weave your points into answers. Your goal is their decision, not your slide order.'
The real objective of a first investor meeting is simply to get a second one, Cummings added.
However, founders should also be mindful of their most limited resource: time. Chasing too many investors can be a distraction. If a startup can grow through customer revenue, more VC calls don't always mean more value, according to Bartolome.
'Some founders schedule 200 VC calls,' Bartolome said. 'If customer revenue can fund you, focus there. A few high-probability VC calls beat 200 low-probability ones.'
To avoid dragging out fruitless conversations, Bartolome recommended clarity.
'[Ask] timeline questions,' he said. ''When do you issue term sheets? 'When should I follow up?' If they can't answer, treat it as a soft no.'
Sometimes, though, getting a fast 'no' from a potential investor can be a blessing in disguise, according to Shelly.
'I push to 'no' quickly,' Shelly said. 'After one to two meetings, I ask check size, timeline, [if they] lean yes or no. If no, I drop them to annual updates.'
Tailor your pitch to the audience — while staying authentic
Founders tend to perfect their pitch for investors, but often forget how crucial it is when talking to potential employees. This, too, is a kind of sale.
'I ask about capacity and willingness for early-stage hours,' Shelly said. 'Be explicit so misfits self-select out.'
Regardless of who a founder is pitching to, authenticity matters. Panelists emphasized that a founder's story isn't just about the company – it's about why they are the right person to solve a problem.
'My founder-market fit is personal. I'm building for women like me,' Shelley said. 'That authenticity carries across investors, employees, customers.'
By the end of the panel, Wright offered a final takeaway of lessons for the audience.
'Simplify your pitch, tell authentic stories, push for clear timelines,' Wright said, 'and be intentional in every conversation.'
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I think there's going to be a lot happening in Jacksonville, and just excited to play a part of it.
