When Darren Berkovitz appeared on the En Factor podcast, he discussed his journey as co-founder of Telesign, which specializes in the 2-Factor authentication that we all use daily. Since then Darren has worked on a number of ventures. He is the Managing Partner for Dear Mama Coffee, serves as an Innovator in Residence for USC Viterbi’s Incubator for technology startups and is working on a new venture: FaceSign – Authentication for the new world.
In his initial episode, he talked about persistence like most entrepreneurs do—as an overriding value, a fundamental principle of success. He emphasized mindset over technical skills. He spoke about the importance of a genuine “why.”
All true. All important.
I recently reconnected with him to find out what he has changed in his journey since his initial episode aired. What has he learned since then? That knowing these principles and living them are completely different experiences.
The Gap Between Theory and Reality
I asked Darren what moment made him think, “This is way harder than I made it sound.”
His answer was immediate: getting clients.
“You think you send a few emails or put a few ads and you get clients,” he told me. “But it often involves complex political and psychological processes to arrive at a buying decision.”
This isn’t the sanitized version of entrepreneurship you hear at conferences. This is what actually happens when you’re in the trenches trying to close deals.
Darren shared a specific example that still stings. He had a prospect say yes. They confirmed they had authority to buy. Everything was lined up.
Then someone above them—someone Darren didn’t even know existed—overruled the decision. A competitor had already built a relationship at that level.
The deal was dead.
When Persistence Gets Tested for Real
“I was thinking, how did I not know about this?” Darren said. “Was the person lying to me that they had the authority?”
They weren’t lying. They genuinely didn’t know the higher-ups had views on the project.
This experience fundamentally changed how Darren approaches client acquisition. He learned that organizational charts don’t tell the truth about who holds power.
He explained how it is subtle. “You see who people refer to on decisions, who has upward mobility, commands authority. Sometimes it falls out of the chain of command.”
When asked what it costs him to map out these political dynamics for each potential client, his answer was honest: “It costs time and energy to do, but the alternative is much worse. This is necessary for big deals.”
He learned this lesson the hard way—by losing deals.
The Moments When You Almost Quit
Darren discussed how there are many moments when he almost gave up on persistence altogether.
“Many times of trying to sell and running into brick walls.”
So what kept him going? Not the motivational poster answer—the real one. The belief that the product he was willing to sell would actually help and solve problems for them.
That genuine “why” he talked about in our original podcast. It came back to that.
The Productive Kind of Stupid
Darren described something most entrepreneurs feel but rarely articulate. There’s an element of persistence that’s almost irrational. Logic would tell you to quit. Something else keeps you pushing.
“Not exactly sure what kept me going—have to be kind of stupid.” That phrase stopped me.
But here’s where it gets complicated. How do you know when you’re being productively “stupid” versus just stubborn about the wrong thing?
“Yes, I have,” Darren admitted when asked if he’d ever stuck with something too long. “It’s very hard to tell and hard to tell by asking for feedback externally. Most people will tell you what you want to hear or be overly negative, and they will never have the full context and experience that you do.”
You can’t trust external feedback because people either sugarcoat it or don’t have your full context.
You’re essentially alone in making that call.
When Intuition Is All You Have
I asked what internal signals or metrics he uses now to know when to persist versus when to quit.
“It’s intuitive. I’ve gotten it wrong many times.”
This is the part most people don’t talk about. Darren has gotten it wrong many times. He’s folded when he should have held. He’s held when he should have folded.
On the podcast, he emphasized mindset over everything. But now he’s learned that mindset alone doesn’t always give you the right answer.
“Yes, this is very challenging,” he said. “Sometimes the right answer only comes from hindsight. The only word I have for it is intuition.”
You only really know if it was right in hindsight.
That’s a tough place to operate from.
What He’d Tell Entrepreneurs Now
I asked Darren what advice he’d give today that he didn’t say in our original conversation.
His answer cuts through all the noise about persistence and mindset:
“Only you can make the call. It’s okay to ask for feedback and take it into consideration based on the source, but only you can make the call in the context of how much you trust yourself and your intuition.”
Darren’s experience reveals something deeper about that mindset.
It’s not just about having the right attitude. It’s about developing the intuition to know when to persist and when to pivot—and accepting that you’ll sometimes get it wrong.
The Real Cost of Persistence
Persistence costs more than time and energy. It costs you the comfort of certainty. It requires you to make decisions without complete information, to trust yourself when external feedback is unreliable, to be “kind of stupid” in ways that might look brilliant in hindsight or foolish.
Darren’s journey since his podcast appearance shows us that entrepreneurial wisdom isn’t static. It evolves through experience. The principles he shared originally—genuine “why,” persistence, mindset over technical skills—remain true.
But now he understands them at a different level.
He’s learned that getting clients involves complex political and psychological processes. That organizational charts lie about where power really lives. That persistence sometimes requires an almost irrational commitment. That you can’t always trust external feedback. That intuition is your only guide, and you’ll get it wrong sometimes.
And he’s learned that only you can make the call.
This is what experiential intelligence looks like—the collective wisdom that comes from living through challenges, not just talking about them. It’s what makes the difference between knowing entrepreneurial principles and truly understanding them.
Darren’s still learning. We all are. That’s the point.
If you would like to connect with Darren, you can do so through is LinkedIn here.
Note: A first draft of this article was written using AI.
