Founder's Journey: The Art of Getting to Yes

When faced with a problem, have you surrounded yourself with people who obsess about risks or with people who relentlessly identify creative solutions?

Being in “builder mode” again, I’m fixated on this question because after 17 years of watching companies from the investor side, I've observed that successful startups are essentially "getting to yes" machines, while most large corporations have evolved into sophisticated "getting to no" operations.

This isn't a character flaw in big companies – it's often rational behavior. When you're managing billions in revenue and thousands of employees, the downside of a major misstep can be catastrophic. Decision makers get promoted for avoiding disasters, not for taking bold risks that might pay off.

Walk the halls of any Fortune 500 company and you'll encounter well-meaning professionals whose primary job has become risk minimization rather than risk management. Legal says it's too risky. Compliance worries about regulatory implications. Finance questions the ROI. The marketing department has concerns about brand impact. IT cites security vulnerabilities.

Each "no" is defensible in isolation, but collectively they create an organizational immune system that rejects innovation. Employees quickly learn that pushing boundaries might get you noticed (not in a good way) while playing it safe keeps you employed. Most decision makers in bigger companies can earn 80% of their bonus every year by simply saying "no" to everything new or risky.

Here's what Founders need to internalize:

The real risk isn't trying something that might fail. The real risk is failing to try things that might work. Getting to "no" means everyone should just go home. Getting to "yes" means you get to learn whether your ideas have merit.

The key insight? Your goal as a startup should be to "get to no" quickly from conventional sources, then regroup and figure out creative solutions. Don't waste weeks trying to convince risk-averse industry veterans to surface creative solutions. Accept their "no" as valuable data and move on to finding unconventional paths.

This is where the magic happens for exceptional startups.

The difference isn't just persistence or optimism. It's a fundamental belief that for every "impossible" problem, there's a legal, compliant, and viable solution that simply hasn't been discovered yet.

The best startups don't just have great teams or better incentive structures. They have Founders who genuinely believe that "no" is just another word for "not yet solved." They approach regulatory complexity not as a wall but as a puzzle. They view technical limitations not as roadblocks but as design constraints that force creative solutions.

The most successful Founders I know were the ones who looked at problems everyone else considered impossible and instead of asking "Can this be done?" they asked "How can this be done?"

That subtle shift in framing makes all the difference between building something incrementally better and building something that changes the game entirely.

Onwards and Upwards.

June 11, 2025