How many follow-ups would you send before giving up on your dream customer?
Three? Five? Maybe ten?
Well, Harry Stebbings sent 53 emails to Marc Benioff, the CEO of Salesforce.
And for 52 weeks, he got absolutely nothing.
Not a single reply.
If you don't know Harry, he's the founder of 20VC, one of the most influential venture capital podcasts, and the man behind a VC firm that raised a $400 million fund.
He started his podcast at just 18.
I've known of Harry since my student days in London, back when I was struggling to sell the first subscriptions to my startup, Jammy, while he was already making waves in the startup ecosystem.
And his approach to cold outreach is a masterclass in persistence.
Here's what he did:
Every Sunday evening, at the same time, Harry emailed Marc Benioff asking him to appear on his podcast.
But he didn't just send the same boring "Just following up" message 53 times.
He did his homework.
Every email included a different, highly personalized P.S.
Benioff's favorite whiskey
His favorite vacation destinations
His food preferences
Salesforce's latest quarterly results
Personal details that demonstrated genuine research
He even A/B tested different approaches.
The result after 52 weeks? Absolutely nothing.
Until one particular email mentioned Benioff's favorite Macallan whiskey.
And suddenly, Marc replied.
He agreed to appear on the show.
Benioff later acknowledged that Harry had emailed and texted him nearly 100 times before getting a yes.
His conclusion?
"Persistence pays."
And that's the lesson for startup founders.
Especially if you're selling to mid-market or enterprise customers with a relatively small target account list.
You can't afford to give up after a couple of unanswered emails.
But here's the important distinction.
Persistence isn't sending the same message over and over. It's finding a new reason to be relevant every time.
My favorite GTM formula for 2026:
Founder-Led + Signal-Based + Multichannel + Creative Storytelling + AI
Research your accounts. Understand their priorities. Find meaningful signals. Make every interaction count.
And respect clear boundaries. Persistence should never become harassment.
Now open your CRM and look at your biggest opportunity.
How many attempts did you make before giving up?
Because Harry was apparently just getting warmed up.
Harry Stebbings on LinkedIn:
https://www.linkedin.com/in/harrystebbings/
20VC:
https://www.20vc.com/
#FounderLedSales #B2BSales #ColdOutreach #HarryStebbings #StartupGTM #Entrepreneurship #Shorts
YouTube / ABVX