By Mark Macias
Founder of MACIAS PR | Former NBC Executive Producer
Brian Cohen was Pinterest’s first investor. I was fortunate to attend a private dinner with him when he shared some advice with entrepreneurs in the room. It was impromptu so I had to take notes on what I had in front of me.
I’ve heard a lot of speeches about entrepreneurship over the years. Most follow a familiar script: work hard, believe in yourself, build a great team and never give up. Brian’s advice was different.
It was blunt and at times almost contradictory. Tell people when their ideas suck. Listen carefully to words. Don’t confuse execution with timing. Shoot for outcomes that seem statistically improbable.
Here are the 8 takeaways I took from that dinner.
The Best Way to Figure Something Out? Question Everything.
Entrepreneurs are constantly being told to have conviction. Brian’s point struck me as the other side of that equation. Conviction shouldn’t become an excuse to stop questioning your assumptions.
The dangerous moment for an entrepreneur may not be when other people stop believing in the idea. It may be when the entrepreneur becomes so emotionally invested that he or she stops challenging it.
Questioning an idea isn’t a sign that you don’t believe in it. It may be how you make the idea strong enough to survive.
Invest in People Who Figure It Out
Brian didn’t say invest in people who already have everything figured out. He said invest in people who figure it out. That’s an important distinction.
Startups operate with incomplete information – something startup founders learn quickly. The original product will change. The customer might be different from the one in the business plan. A competitor comes out of nowhere. The economy shifts. You can’t possibly anticipate every obstacle before starting.
So perhaps one of the most valuable qualities in an entrepreneur isn’t having all the answers. It’s demonstrating the ability to find an answer when reality changes the question.
“Your Idea Sucks” is More Valuable than “Great Idea”
Brian said most people want to be nice. And that hurts entrepreneurs.
Friends tell you an idea sounds great. People don’t want to create an awkward moment. Brian’s philosophy was essentially: don’t coddle people. If the idea sucks, tell them.
Of course, there’s an important difference between being cruel and being candid. False encouragement can be expensive in business. If an entrepreneur spends two years and hundreds of thousands of dollars pursuing a flawed premise because everyone around them was too polite, nobody did that entrepreneur a favor.
The same principle applies inside established companies. If everyone in the room agrees with the CEO, that may not mean the CEO has an extraordinary idea. It could mean the company has built a culture where disagreeing is uncomfortable.
Good ideas should be able to withstand difficult questions.
Be Annoying
I don’t interpret that as permission to harass people or ignore a definitive no. I took it as an argument for persistence beyond the point where most people become uncomfortable.
There are countless socially acceptable reasons to stop pursuing something. They didn’t respond. The meeting didn’t happen. The investor passed. The customer wasn’t interested. Someone told you the timing wasn’t right. Persistence means determining whether the answer is genuinely no or merely not yet. It’s a question we face nearly every day at MACIAS PR.
A reporter declining a story today doesn’t necessarily mean the underlying idea is permanently dead. The news cycle changes. New data emerges. The company evolves. Persistence combined with intelligence can create opportunity.
Listen to the Words People Actually Use
Entrepreneurs are salespeople by necessity, and good salespeople tend to be optimistic. That can become dangerous when optimism starts translating ambiguous feedback into validation. “Interesting” doesn’t mean I want to invest.
People frequently tell us exactly what they think, but we unconsciously translate their language into the answer we wanted. Listening to customers, investors, employees and journalists—can reveal information that enthusiasm causes us to miss.
What Is the Biggest Factor in Startup Success? Timing.
Market timing deserves more attention than it usually gets because entrepreneurs love the idea that execution determines everything. Execution is something we can control. Timing isn’t.
You can build an excellent product and still arrive before consumers are ready for it. A mediocre idea entering a rapidly expanding market can sometimes have advantages that a brilliant idea entering a stagnant one does not.
Of course, that doesn’t make execution irrelevant. It means execution happens within a larger environment. The entrepreneur has to ask not only “Is this a good idea?” but “Why is this a good idea now?”
Be Darth Vader
Angel investing is built around an uncomfortable mathematical reality: many investments won’t produce extraordinary returns. A small number of winners can drive an enormous portion of the outcome.
Cohen knows that firsthand. Pinterest was his extraordinary hit. The lesson I took from his Darth Vader comment is that if you’re taking the enormous risk required to build something from nothing, incremental ambition may not justify the risk.
Not every company needs to become Pinterest. But entrepreneurs should understand the size of the opportunity they’re pursuing before dedicating years of their lives to it.
Luck Matters. But You Can Influence Luck.
Entrepreneurs understandably don’t like attributing success to luck. It can feel as if luck diminishes the years of work, sacrifice and judgment that went into building something. But pretending luck doesn’t exist doesn’t make us more sophisticated.
You can’t control whether you happen to meet the right investor at exactly the right moment, or every economic cycle. What you can control is how many opportunities you create for luck to find you. Question the assumption everyone else accepts.
If one potentially transformative encounter has a tiny probability of happening, increasing the number of meaningful encounters increases the surface area where something unexpected can occur.
Cohen’s bigger takeaway is definitely valuable to every entrepreneur and as the founder of this PR agency, I’m happy to say we integrate his thoughts and approaches into every media campaign.
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About Mark Macias
Mark Macias is the founder of MACIAS PR, an earned-media public relations agency specializing in media coverage, media relations and thought-leadership campaigns for healthcare, technology, AI and financial companies. Before founding MACIAS PR in 2009, Mark was an Executive Producer with NBC and Senior Producer with CBS in New York, where he evaluated and approved story ideas. His newsroom experience now shapes the media strategies MACIAS PR uses to identify newsworthy angles and secure earned media coverage for clients.