PPPPlace Your Bets (Four Ps #241)
Knowing when to hold, fold, walk away, and run in business and life.
On a warm summer's evening, on a plane bound for… somwehere, I thought of "The Gambler."
Too tired to sleep, I opened up my laptop, tried to access wifi without any luck.
So I just stared out the window at the darkness, thinking about the young men who are now "rawdogging" flights. If they make do it, so could I.
Barely.
Fast forward a few hours, the wifi connectivity at the hotel was also not working (or occasionally working at the speed of my old 14.4 dial-up internet connection in the days before LAN connections in my college dorm room).
A hotel without suitable wifi? The horror! The thought is enough to make the most hardened digital professional shake like my 10 year-old washer-dryer unit.
I could have complained. I could have asked for another room. I could have asked for a discount. I could have switched hotels. Or I could just "rawdog" it for an entire week.
But the purpose of professional networking events is to meet people. Get out of your room. Work the floors (or in the case of Cannes: hit the yachts and villas), Not to stay in your room.
Making good decisions comes with experience.
As Kenny said in what has become one of the most popular karaoke songs of all-time, "You've got to...
THE PROFESSIONAL: "Know When to Hold 'Em..."
In the fast-paced world of Artificial Intelligence, knowing when to dive in or wait is more critical than ever for nearly every business. The key to innovation is balancing the “thirst for first” with measured patience.
Premature development and rushing solutions to market can backfire with consumer trust.
Waiting too long could mean falling behind the competition.
However, in a world where AI advancements, tools, and impacts are accelerating faster than a New York Mets playoff push, this balance is even trickier than it sounds.
On one hand, it feels like everyone is pulling back on the throttle just a bit.
According to Lucidworks, the adoption of generative AI in enterprises has hit a speed bump. Why? Accuracy and cost.
Manufacturers are sweating bullets over the accuracy of GenAI outputs—a legitimate concern that can lead to catastrophic consequences if not handled correctly. Lucidworks’ CEO, Mike Sinoway, points out that only 60% of manufacturers plan to boost AI spending this year, down from 93% last year.
But while cost and accuracy are formidable barriers, they are not insurmountable. Venture capitalists are still investing heavily in AI startups, betting big on a breakthrough that will iron out these kinks.
This tug-of-war between cautious optimism and looming skepticism is the current state of the AI game.
On the flip side, CMOs worldwide are not exactly folding their AI cards. Stacked Marketer reports that only a timid 6% of CMOs have zero plans to adopt AI in the immediate future. The rest are either already integrating AI, planning to do so soon, or exploring future options.
The message is clear: AI isn’t just the latest shiny toy; it’s a strategic tool that, when used wisely, can deliver serious benefits.
But let’s cut through the hype. AI isn’t about jumping on the bandwagon just because everyone else is. It’s about finding the right problems to solve and leveraging AI to drive meaningful outcomes.
This means looking beyond the tech itself and focusing on the benefits it can bring both internally—streamlining operations, enhancing decision-making—and externally—delivering better customer experiences and creating value.
So, while you can subscribe to 50 AI-themed daily newsletters or bury your head in the sand and hope it just goes away, there's a more surgical approach. Don’t rush blindly towards the finish line. But don’t sit on the sidelines either. Assess the terrain, understand your challenges, and deploy AI where it truly makes a difference.
The trick isn’t just knowing when to hold 'em or fold 'em... It’s knowing why.
In essence, balancing the speed of AI adoption is like playing a strategic game. Move too fast, and you risk stumbling. Move too slow, and you might fall behind. The real skill lies in making informed, deliberate decisions that align with your business goals and customer needs. Ready to gamble?
THE PRACTICAL: "Know When to Fold 'Em..."
While many of us, myself included, like to talk about our successes — the big deals, the startups that made it, the small teams that grew into powerhouses — few of us share the stories or lessons of our failures. If we can even call an unsuccessful product launch or bootstrapped company a failure.
Having worked with nearly half a dozen early-stage companies, and worked with a dozen more in a consulting, advisory, or contract basis, there's a right kind of wrong... or smart ways to fail well.
So, let's embrace the chaos, my friends. If there's one thing startups taught me, it's that failure is not only inevitable but essential. Think of it as your secret weapon.
This counterintuitive idea that embracing failure is essential for driving innovation and long-term success in organizations is fundamental for ANYONE who works at a start-up or early-stage company at any level. Some key scars:
Fail Fast, Learn Faster: Not every product or service is going to be an instant hit. It's like a pharmaceutical company investing millions in R&D. Trials bomb, but you have to analyze the failure, pinpoint a flaw in the research, fix it, and eventually develop a drug that saves lives. Moral of the story? Fail fast, learn faster. Treat every failure as a stepping stone rather than a stumbling block.
Create a Blame-Free Zone: When the Web3 bug hit a few years ago, I joined an early-stage blockchain company that built a foundational model for how companies still use blockchain today. What made the initial product so great... along the way, we learned that input fuels improvement. When people aren't terrified of ridicule, they innovate. Encourage your team to take risks and share their "ugly babies." You'll be amazed at what can come out of a blame-free zone.
Understanding the Spectrum of Failure: Not all failures are created equal. There’s a spectrum. On one end, you've got negligence (a construction worker ignoring safety rules). On the other, you have brave experimentation (a dev team trying a new code to enhance user experience). Distinguish between these to foster a culture that celebrates intelligent risks and learns from them.
Psychological Safety: Ever been in a meeting where you were too scared to share your ideas? Now, imagine a meeting where everyone feels safe to speak up. I've been in both environments and which one do you think breeds innovation? Exactly. Psychological safety is your best friend. Model curiosity, admit your mistakes, and welcome dissenting opinions. Create an environment where ideas flow freely, without fear of reprimand.
Strategies for Learning: Post-mortem reviews are your golden ticket. After a flop, gather the team, dissect what went wrong, and brainstorm improvements. One of my teams once had a sales pitch that went so badly that the client lead literally asked the team to leave before the meeting was over. But it was a low point, not an endpoint. We debriefed and learned from it. Encourage experimentation and calculated risk-taking. Share the lessons across the organization. And for the love of all things good, celebrate those healthy failures! When your team feels safe to fail, they’ll feel free to succeed.
A Culture of Feedback: In a thriving startup, feedback is as routine as morning coffee. Celebrate calculated risks and the lessons they bring. Reward innovation, even if it comes cloaked in failure. Regular check-ins, peer feedback, and open dialogue about setbacks can turn your team into a powerhouse of continuous improvement.
When to Quit: When building a youth sports social network in the late 2000s, we had a dream team, a dream product, and the right partnerships. As laws were passed about how to engage with kids online, it required pivoting, patience, cutbacks, and ultimately a premature sale. Knowing when to shut things down, and having the courage to do so, meant saving value and walking away without a loss.
In the end, the right kind of wrong is your best path to success. Foster a culture of psychological safety, distinguish between types of failures, and implement strategies to learn from every misstep.
By doing so, you'll not only drive innovation but also create a motivated, engaged workforce ready to tackle any challenge. Now go forth and fail smartly!
THE POLITICAL: "Know When To Walk Away..."
I love Joe Biden. He's such a good, genuine human being, perhaps the most authentic, honest president we've had in my lifetime.
As a supporter of President Joe Biden, I have the utmost respect for his service and dedication to our country.
At the timing of this writing (Mon, July 15th at 10pm ET), Biden is still in this race. He hasn't withdrawn, stepped aside, or even hinted at backing down.
Though that doesn't mean he's still in this race.
He had an underwhelming press conference last week, and then the assassination attempt on Trump has put Biden’s candidacy in an even more precarious position. Even before the horrific display of American gun violence took place over the weekend, Trump was the favorite. Now his status as front-runner is secure.
And therein lies the biggest threat to democracy at the moment.
For the good of the nation, it is time for him to step aside and let a new leader take the helm of the Democratic Party. While there is significant division among the Democratic Party at the moment whether to stick with Biden or move on, the upcoming election is crucial.
And it's clear now that even despite last week's impressive press conference (which he likely rehearsed for days on end), Biden's age and health are undeniable factors that could hinder his ability to win.
A Trump victory would undo decades of progress and set our country back a hundred years. We have seen the damage that his presidency inflicted on our democracy, civil rights, and international standing. Allowing him to return to office is a risk we cannot afford to take.
Our focus must be on preventing this outcome at all costs, and as such, there's no shame in quitting (my post).
While there is no clear alternative to Biden, Governors Gavin Newsom and Gretchen Whitmer stand out as viable options. Both would trump Trump in a debate, both in mental and physical impressions.
Transitioning the nomination is complex, but Biden releasing his primary delegates and directing them towards a unified choice (he'd probably favor Vice President Kamala Harris) would pave the way.
A convention floor vote would be a historic event, reminiscent of the spirited, decisive conventions of a century ago. Such an event, while daunting, could reinvigorate our political process and engage voters in an unprecedented way. The thought of this both excites me and terrifies me, but it would be the most incredible event in the history of modern technology. There has not been a meaningful convention floor vote since the 1960's, before widespread live TV and social media.
100 years ago, convention votes often went 20 or 30 votes before there was a consensus pick to lead a ticket. They could last for days. Wow.
The Democratic Party must prioritize rallying independents and swing voters. The anti-Trump sentiment among Biden voters is strong, and they will likely support any Democratic candidate. Now, the focus must be on capturing the hearts and minds of those who are undecided. We need a candidate who can bridge divides and appeal to a broader spectrum of the electorate.
President Biden's legacy is secure, and his contributions have been invaluable. Many don’t want him to step aside (and I don’t expect him to at this point), but the bigger picture may require it. However, for the sake of our nation's future, it is imperative that he steps aside and allows a new leader to emerge who can unite us and lead us forward in these challenging times.
THE PERSONAL: "...Know When To Run"
This is a hard one, but in the spirit of transparency, here we go.
I loved sleepaway camp. I wanted my kids to go ever since I could remember.
My older son was never interested, but my daughter is very much one of those kids who goes where the crowd goes.
Here in the northeast United States, a large percentage of kids aged 8 to 15 go away for 4 to 7 weeks at a time. Last year was my daughter's first summer away. She had a generally positive experience even with some homesickness and a few health-related hiccups.
In Year 2, her pre-departure build-up and nervousness were higher than last year.
"It's normal," I thought.
Tears upon departure.
"It's normal," I thought.
Letters home in the first few days that let on a level of homesickness that exceeded last year.
"Still normal."
But then we got phone calls from counselors. She was having trouble sleeping and other health-related issues were popping up.
"They can handle it," I told my wife.
But after the second week, things were getting much worse.
"Let's give it a few more days. Visiting Day is next week."
The days leading up to Visiting Day Weekend were incredibly hard. Letters sent talking about how she hated it at camp, outlining the issues she was having, asking to come home, and the toll it was taking on her body and her mind.
And that's when my thinking changed. I thought again of "The Gambler." You don't always know... until you know.
Seeing her made the decision easier. So it was time to run. To get our girl. To take her home. She was legitimately sick, and unfortunately continues to be days later. Sicker than the camp either let on or actually knew.
Summer camp is supposed to be fun. Challenging, but rewarding. A time for growth, independence, and social development. Cooperation, friendship, sportsmanship, and even confidence-building.
But if that's not happening, what's the point in staying?
Credit to my wife for recognizing it early on, earlier than I was ready or able to. (Our spouses are always right, aren't they?)
So here we are, a family of four (plus the dog) reunited again at home for the summer.
We're already finding local activities for her and she'll be fine, already resting and recuperating. And while I'm still somewhat disappointed that it didn't work out for her, I'm relieved she's not suffering through it anymore, or allowing physical or psychological trauma to accrue.
While she'll miss out on some valuable lessons from being away, knowing that we're here for her when she asks for help is the greatest lesson we could possibly share with her...
