August 2025

Many of us know the stories by heart: Twitter started as a podcasting platform, Instagram began as a check-in app, and Slack evolved from a gaming company's internal tool. The most successful companies don't settle with roadblocks—they transform because of them, constantly evolving until they find their perfect market fit. We celebrate startups for their agility.

While we applaud business evolution, as humans we are strangely resistant to our own personal reinvention. As AI reshapes entire industries and threatens to automate countless roles, many of us remain complacent. We're comfortable with startups pivoting overnight, but when it comes to our own careers, we move much slower. This reluctance to change will hinder our ability to maximize our careers.

This is precisely why I'm thrilled about our AI Learning Journey at StartupExperts. Over the past 6 months, nearly 1,500 individuals have participated in our programs, actively working to improve their AI proficiency. In many cases, we're focusing on reskilling people mid-career in preparation for a future with AI. It's been incredible to observe a number of attendees embrace the mindset that successful startups have mastered: the willingness to learn, adapt, and evolve.

But what excites me even more is watching the next generation approach this challenge differently. My teenage daughter, Colbie Freese, launched her own company a year ago called Shine! Girls Leadership, and she's taking a different approach. Rather than needing to reskill existing professionals, she's focused on properly training girls from the ground up. By partnering with Apply AI and other organizations, she's developing a comprehensive three-part training course specifically designed for teenage girls.

This September 7th, Shine! Girls Leadership and Colbie will host their first training session called “AI in Action” and they will welcome any teenage girl who wants to become more knowledgeable about AI and how to use it. This program is focused on developing the next generation of women leaders who will be AI-native from the start.

Here's where I need your help - we're looking to spread the word about this program. Colbie is seeking to find teenage girls who want to participate, but also teenage girl leaders who are interested in forming their own cohorts and co-hosting training sessions. If you know a teenage girl or work for an organization with parents of teenage girls, can you please take 5 mins today to spread the word?

In the Guest Post section of this Field Guide, Colbie shares more about the Shine! Girls Leadership program, why she is passionate about this training, and even has drafted an email that you can forward along.

Unlike the rest of us who need to be re-skilled, this is an opportunity for teenage girls to be trained correctly from the beginning and become leaders in the AI world. I also feel that this is a chance to come together as a community and help shape the next generation of women leaders. Thank you for your help!

With warmest wishes, Jesse

DISCLAIMER

The opinions in this newsletter are solely my own and don't represent any affiliated organization's views. Information is provided for general purposes only without warranties regarding accuracy or completeness.