Those who know me are aware that a significant portion of my professional life had revolved around travel. From 2009 to 2020, I constantly found myself either relocating to another state or country, or boarding a plane for business meetings and conferences.

The last three years 

I vividly recall a conversation with my former boss in January 2020. I expressed how exhausted I was and how the relentless travel was taking a toll on my well-being and my physicality.   He assured me that we would monitor my travel more closely that year, but despite our intentions, I was still booked for travel during 9 out of the first 12 weeks.

After my third trip of the year in early February 2020, the world began to shift, and trips began to get cancelled. We are all well aware of the impact the pandemic had on travel.

While the pandemic brought about one of the most challenging periods for many of us who traveled, I found it difficult to complain. It granted me the opportunity to spend more time at home, prioritize my health (resulting in a life-changing weight loss of 80 lbs) and contemplate how I wanted to shape the next few years of my life.

During this time, I also welcomed a new addition to my family—a dog named Bucky. I dedicated some effort to improving my golf game (although my handicap has unfortunately risen again!), and I found myself dating a wonderful woman, despite previously telling my colleagues that I was undateable due to my overwhelming travel commitments.

I was relishing this newfound stability so much that when things began to open again, I made the decision to leave my job in July 2021. I believed it was time to avoid getting back on the road and instead attempted to acquire a local insurance agency near my home. My plan was to reconnect with my roots in intermediary distribution and establish a business closer to home, allowing me to travel solely for leisure. Unfortunately, that endeavor did not pan out due to various reasons (I’d be happy to share the story with you in a chat!).

Concurrently, I ventured into the world of independent consulting. Over the past two years, my consulting business has done well, having worked with a global-leading reinsurer on embedding third party solutions into their reinsurance value proposition, a multi-line carrier on assessing their innovation practices against the market and how to accelerate innovation adoption internally, and multiple insurtechs on both market entry and how to navigate prospective buyers and investors.  Being independent has evolved into some new opportunities as well (stay tuned for updates in the coming weeks!).  

Despite engaging in numerous video calls each day and managing to stay connected with people, I couldn’t help but feel the absence of genuine human connection.

Insurtech Insights played a vital role getting me back out there

When Ciaran invited me to speak and I started collaborating with Emil and Midori on panels, I knew it was time for a dedicated week in New York to connect with as many people as possible.

The joy of having one-on-one meals with individuals I had previously conversed with only virtually, or the dinners with old friends (including the one I unfortunately missed, but still received toasts in my honor, as I was later told), reminded me of the irreplaceable value of personal interaction.

The conference itself

Overall, I found this conference to be exceptionally well-organized:

• The networking app was efficient, while the matchmaking area was lively and bustling, 
• The booths were well-spaced out and not crammed together,
• The panel discussions were highly attended and engaging (despite one of my own panels competing at the same time with Coach Primetime’s session!), 
• There were publicized after-conference events typically reserved for the privileged few, and 
• The additional touches, such as having a hairdresser, coffee station, and live music entertainment, added a nice flair to the overall experience.

Moreover, witnessing the success of a few Insurtechs I had been following for years was truly inspiring. Among the notable conversations I had were those with:

• Paul Gagliotti, who told me about some recent successes for Harbor.ai in his business.  We also spoke highly of Ali Ahmadi and TCARE’s exceptional performance (and expedition of Mount Everest),
• Adam Erlebacher, who has been flourishing since his exit to W&S, and 
• Bobbie and Brent from Benekiva, who I remember passionately sharing their vision in Chicago back in spring 2018, and now, having continued success, including securing a massive partnership with one of the world’s leading reinsurers.

And lastly from a content perspective:

• Most everyone was talking about Generative AI, it’s impact within the value chain, how they were testing it, and possible regulatory considerations with different use cases (specifically underwriting/risk assessment),
• The two panels I moderated on the future of fleet insurance and big tech/insurer collaboration were both very lively discussions and well attended,
• Funding pressures are real, for both startups and investors. And while there is dry powder out there, many expressed it’s not as easy to get a deal done in this environment, 
  • Companies that were too highly valued and now not valued as high (or not at all), are making it tougher for new companies trying to raise,
• And, there continues to be an influx of individuals leaving the corporate world to start their own consulting firms and be more in control of their time.

No matter how we individually experienced the conference, it’s ultimately the people who keep us coming back. We all have those individuals we rely on as our conference buddies or bailout options. To those who fill those roles for me, you know who you are, and I am immensely grateful for your presence.

My own reflection

Just before boarding my flight to New York City last Monday, I called my mother from the airport and confidently told her, “I don’t miss this.” She responded, “Really? This used to be your life. It’s big of you to say that.” I replied, “Yeah, but I love my life at home.”

Well, as moms often are, she was right to some extent.

I did miss it. Not the travel itself or the airport chaos (especially with all my status benefits gone).

This event felt as a great re-integration for me back into the community at large.  This doesn’t necessarily mean I’ll be on the road 180 days again like I was in 2018 or 2019, but I will be more present and flexible.

The Insurtech community in SoCal/LA is vibrant, and we have a great investor and insurtech community here (Eos, Clocktower, Brewer Lane, BMI, Pavo, BuddyIns, Phonexa, Hazard Hub amongst others!).  Perhaps it’s time for us to gather more frequently (kudos to Brett and Gilad for holding down the fort thus far!).  

Final thoughts

I am cautiously optimistic for the rest of the year and going into 2024.  Partnership and investor deals are being done, albeit with much more scrutiny.  It’s ever more important for buyers/investors to effectively communicate the problems they are facing so that insurtechs/suppliers can effectively communicate the solutions that they provide.

The power of each of our individual and organizational networks is what will help us navigate this environment over the coming months and help get deals done.

If you are an insurtech needing help in telling your story to buyers/investors, a reinsurer or carrier needing help in prioritizing key initiatives and/or getting a key project over the line, and/or an newly independent consultant trying to learn ropes better and what to and not to do, give me a call.  We are all in this together!

And thank you to Heather, Janene, Marissa and Jane for the pics since I didn’t take many at the conference!!!