Up and In Daily Recap: Culture, Capital & Calculated Risks

This past week on Up and In Daily, we dove into the intersection of sports culture, venture capital, mindset, and modern betting strategy. It was a week that reflected the tension between innovation and introspection — between future-forward business moves and present-moment personal growth. I threw out some picks for the sports betting degens, talked about some of my favorite athletes and their futures, and got really real. Lets recap.

Pikkit: The Sports Betting Tool You Needed

Pikkit isn’t just a sports betting tracker — it’s a game-changer for anyone who wants to treat betting like a real portfolio. With BookSync technology, it syncs your bets directly from sportsbooks and gives you real-time performance analytics, line shopping comparisons, and even access to the betting moves of top users.

As someone who takes a disciplined, data-driven approach to sports betting, Pikkit helps me see my plays clearly — not just wins and losses, but the process behind them. I partnered with them because I genuinely believe it makes you smarter.

And with affiliate code RANAUDO, new users can get a mystery bonus between $3–$100 when they link Venmo or PayPal.

Sports betting is evolving into a financial strategy — and tools like Pikkit are leading that shift.

The Gamification of Betting: Fliff & the Future

On one of the shows this week, I dove into Fliff, the rising social sports gaming platform that's reshaping how people think about betting. What’s unique about Fliff is their “play-for-fun” approach that blends social engagement with sweepstakes-style betting, making sports gaming accessible to a broader audience — especially in states where real-money gambling remains restricted.

They’re part of a growing wave of companies trying to turn sports betting into a more casual, gamified experience, something closer to Candy Crush or fantasy football than Wall Street speculation.

Big Moves: Fanstake’s $6.25M Seed Round

Another major story was Fanstake’s recent $6.25 million seed round — a bold move signaling how VCs are still bullish on innovation in sports investing.

Fanstake allows fans to invest in the future earnings of athletes by backing them early in their career — essentially buying a slice of potential upside.

The round included major players like Courtside Ventures, known for backing sports tech disruptors like The Athletic, 100 Thieves, and Religion of Sports. The fund is co-led by Vasu Kulkarni and has a reputation for being at the intersection of sports, media, and consumer technology.

What stood out to me was not just the capital raise, but what it signals — a growing convergence between collectibles, athlete branding, and retail investing. It aligns with everything I’ve been building behind the scenes with The Players Dealer, Vaulted, and Foli — making the fan experience more immersive and financially participatory.

Sports News and Recaps

Washington Nationals rookie Dylan Crews is off to a slow start— however, his advanced metrics—14.5% barrel rate, 40.8% hard-hit rate, and a .323 expected wOBA—suggest he's making quality contact and could see improved results as the season progresses. I may or may not have predicted he is going to go to his first All-Star game this year, and was ROY the favorite when I filmed last week.

In the NBA, following the Lakers' first-round playoff exit, LeBron expressed uncertainty about his future, highlighting the personal fulfillment of playing alongside his son, Bronny, this season. He plans to consult with his family before deciding on a potential 23rd season.

I also spoke on the Bucks' playoff loss to the Pacers and how Giannis Antetokounmpo was confronted by Tyrese Haliburton's father, John, who taunted him on the court. Giannis responded by emphasizing the importance of humility in victory. Tyrese later expressed embarrassment over his father's actions, and John agreed to refrain from attending Pacers games for the foreseeable future. I thought it was such an incredible job on everyone involved and just speaks volumes to Giannis' innate leadership in life, not just ball.

For a further account of the incident between Giannis Antetokounmpo and Tyrese Haliburton's pops, you can read more from CBS here.

Mindset Theme: Get Comfortable Being Uncomfortable

Beyond the headlines, this week was a personal one. I talked openly on the show about making the switch, walking away from security (businesses, routines, expectations), and stepping into something less defined but more aligned.

Whether it was reading The Four Agreements, meditating on The Wisdom of Insecurity, or reviewing my weekly betting model updates — the message stayed clear:

"Growth happens where comfort ends."

I’m betting on myself right now. That means showing up every day — whether that’s filming Up and In, working with athletes in many ways, researching MLB slates, pitching brand deals, or sending in applications to companies I believe in.

This week was a reminder that you can’t script the whole journey.

Day by day baby.

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