🦃 Michelin 3-Star Story, Thanksgiving, and Insurtech
Lolita and Josh at the Inn at Little Washington.

I turned 34 in September, and Josh and I celebrated our 6th wedding anniversary at the Inn at Little Washington’s 3-Michelin Star restaurant on Halloween. It turned out to be both a trick and a treat. The treat was to experience a unique six-course food journey with the man I love with all my heart. The trick was its history and the connection I made to you and me. The Inn got its start in the 80s and a garage, just like me.

Yeah. This three-star Michelin Star restaurant started out as a garage that didn’t do too well as a business and became a candidate for demolition. That was until two extraordinary people, saw the garage’s potential, took a risk, spent their savings, took out a loan, and bought it. They had the vision to create an inn and a restaurant. And that’s precisely what they did. In 1984, the Inn and restaurant opened. Five years later, the Inn at Little Washington became the first restaurant/inn to receive five diamonds from the AAA for both its food and accommodations. Thirty-four years later, in 2018, the Inn received a coveted three-star rating from the Michelin Guide.

The moral of the story: it took extraordinary people to see huge potential, take the risk on something that others were ready to destroy. It took extraordinary people to turn a diamond-in-the-rough into a success that to-date creates great value to others that it is recognized as one of the best in the world.

I see you as my extraordinary people - the extraordinary people who see the potential in me, a woman born in the 80s, and who got her start living in a garage. Your presence in my life and your support allows me to believe that I can create massive value as a human, an operator, and as an investor.

On this month of thanksgiving, I thank you for betting on me and I wish you quality time with your family and friends as we wrap up 2019.

Shout outs
Congrats Arlan Hamilton on her book It's About Damn Time: How to Turn Being Underestimated into Your Greatest Advantage and Matt Wallaert on his book Start at the End: How to Build Products That Create Change; Noramay Cadena for becoming one of Portfolia’s Rising America Fund’s leads; Carmen Palafox, Noramay Cadena, Alex Marshall, and Maria Salamanca for launching the Latinx VC community; Mark Suster for Upfront Venture’s $250M fund; Kobie Fuller for launching Valence, an incredible community built for and by black professionals; Christy Wyskiel for raising and donating $1,000,000 to organizations dedicated to improving education for Baltimore City's children through the Baltimore Next Generation Investing Event; Pam Kostka for bringing All Raise (hiring) to Los Angeles and Boston and helping increase the number of women funders and founders; Elizabeth Galbut and Pocket Sun for launching the SoGal Global Pitch Competition for Women & Diverse Founders, the largest of its kind; and Shervonne Cherry and Jess Watson for launching the Baltimore Womxn in Tech community!

I’d like to continue to shouting out the awesome things you’re working on. If you’ve got something to share, hit reply and let me know.

Work + Life

Aug | Harvard Business School published a case study on Backstage Capital, and I was excited to see my name attached to the story of a venture capital fund that has invested over $7M in more than 120 companies led by underrepresented founders. I also joined the NextGen Venture Partners community, which focuses on investing in early-stage B2B SaaS, digital health, and next-generation commerce.

Sept | I turned 34 and celebrated three months in Baltimore! SoGal Ventures invited me, along with investors from Rise of the Rest and Reflection Ventures, to judge their female-founder SoGal Washington DC Pitch Competition; Vishion, a decor search-by-color engine, won! I was also invited to speak on one of my favorite topics, Raising Inclusive AI, at the Worcester Polytechnic Institute in Boston.

Oct | I celebrated my sixth wedding anniversary to Josh! Technolochicas invited me to Intel in Santa Clara to give coding workshops to middle-school Latinas and speak on a panel with the infamous Eva Longoria. I was happy to see sparks of STEAM curiosity in the girl’s eyes. Technical.ly quoted me in their How Baltimore is working to close the funding gap for founders of color post. Salesforce added me to their Fun Follows on Twitter list. And I saw my good friend, Celia A, one last time before she left to live out to Ukraine.

Nov | I found that an interview I did with Business Rockstars several years ago made it to Amazon Prime Video. Who would have thought?


Death by Meeting | I couldn’t put this book down. It’s an interesting one if you have ever wondered, “can meetings be effective and fun and, if so, how?”

Not Your Perfect Mexican Daughter | This book gives a glimpse into Mexican culture and, my favorite part is that the main character in this book makes it ok (even fun) not to be a perfect daughter.

A List For Your Next Tech-Friendly Book Club | Here is a book list Crunchbase compiled. It includes a couple of my other favs.

Life Hacks

Better sleep + avoid neck pain | My chiro says people’s necks are losing their natural curve - because of our constant use of laptops and smartphones - and that is causing a lot of pain in the neck. It’s true for me. So, I picked up a roll pillow. It’s helping.

Avoiding sinus pressure | I find that sleeping with my humidifier helps avoid waking up with sinus pressure.

Seeing your finances in one place I We’re using Personal Capital to manage our retirement accounts in one place and to access financial advisors. So far, they’ve been helpful. Here’s Josh’s promo link to get 3-months of free financial advisor access and access to a free dashboard.

Finding ways to laugh | Download TikTok and scroll. You’ll laugh, I guarantee it.


Intros to awesome insurtech pre-seed/seed B2B startup founders, in general, and looking for funding. Josh and I are working on an investment thesis around both of our strengths (Insurtech + B2B) and looking forward to making our first early-stage insurtech angel investment.

Intros to companies that need software engineers and are ready to hire.

Big Thanks

Josh T for pushing me to test my limits. Matt W for keeping it real on our calls. Ricky S + Nausheen R for supporting me with my speaking gigs. Pam K for being an ally. Hailley G for inspiring me and introducing me to the Enneagram world. Jim M for lunch and introducing me to aquafitness. Tom I for being a troublemaker and introducing me to delicious coffee. Oscar C for keeping self-care front and center. Dana L and Michele C for showing up in life and work. Mike L for being a risk-taker and connector. Alyssa G, Lisa C, and Ben B for making my part-time VC career possible. Christy W for taking me under her wing and making me feel part of Baltimore’s trailblazer community. Indigogh for getting me to the gym. Ava P and Jess G for being kick-ass founders and allies. Seth F and Katie D for keeping the Global Shaper link alive. Maggie G for helping me execute on my first fundraiser. Thiru V for inviting me to see the real world. Andrew C and Ann C, Jade D and Andrew H, Paige H and Tony H, Shervonne C, Jessica W, and Christian V for welcoming us to Baltimore and showing us around!

Lolita Taub