✨ On "being" in 2020...

Upleveling, shout outs, salt flats, reads, blowdryers, and more!

Matching and hanging out with Tedi 🐻!
January 15, 2020

Hi all, I’m trying new things this year, starting with a new newsletter name/format and showing up as more of me (includes life-size bears and matching outfits). And so much of it has come from Eric, my exec coach, challenging me to move away from “doing” to ‘being” to uplevel, and Monica’s, my sister, #realtalk Sunday Calls.

“Being” is in-progress but definitely not linear. I am standing up for what I believe in more often — calling people out and asking the tough questions people want to ask but don’t — and putting my dreams out there. It’s been hard, exhausting, and, at times, sending me into autopilot mode. But I’m pushing through by reflecting and listening to my community (a lot of whom is my Twitter family, Josh and you).


Congrats! 🍼Cody (Trust and Will) had his first baby. 🧶Ayinde (nēdl) made the list for BuiltinLA’s 50 Startups to Watch in 2020. 💰Samara for launching Chingona Ventures! 🚀Sahil (Gumroad)’s customers crossed $250M in revenue. 📕Henri (Harlem Capital) was featured in a Harvard Case study. 🌟Darren (Workfrom) made the Techstars Anywhere 2020 cohort. 🤩Katherine made partner at General Catalyst. 💥Leslie (Female Founders Alliance) and Irene (Monarq Incubator) are integrating forces. 🥳Jewel became head of Google Startups. 💸Bryan was promoted to General Partner at Backstage Capitals. 👟Payal (Classpass) became this decade’s first unicorn.


Work + Life


Invested in Operators Collective Fund (they have a 90% women and 40% women of color LP base! 🙌🏽); was featured in Decoding Bias in AI 🤖; traveled to the Amazon and the Bolivian salt flats 🧂.

And we made sure to take the mandatory dinosaur 🦖 photo. With the women fighting and the men running. 😂
December 30, 2019
We had a lot of fun taking photos. 📸
December 30, 2019


Was invited to mentor Techstars Anywhere 2020 class + my panel on “Underserved Markets for SaaS Companies” made the 20 Trending VC Sessions list at 2020 SaaStr Annual! Also, Josh and I made our first insurtech angel investment!


Decided to add one more project to my list, a first-time founders (FTF) course; also exploring a FTF dinner series in Baltimore.


🕵🏼‍♂️Secrets of Sand Hill Road by @skupor
Mandatory VC reading. It’s good to keep up with what Silicon Valley celebrity investors are saying to founders and how they see the VC scene evolving. Get it.

🌬Widen the Window by Elizabeth A. Stanley PhD
Boring but helpful in understanding, extending, and leveraging emotional bandwidth. Helpful for execs who want to “really” keep cool when shit hits the fan and make the “right” decisions. Get it.

👍The Likeability Trap by @aliciamenendez
The book should have been titled, “A Women of Color’s Survival Guide.” Great book for women of color who want to “be” and thrive in a society that wasn’t made for and is still marginalizing them. Get it.

Life Hacks

🎧If you lose an airpod pro, you can try to find it with your iPhone, or easily order a replacement. Find out how.

👋🏽Share who you are to find and attract your people. I can’t tell you how many values-aligned people reach out to me after I share what I’m about.

👗Rent the Runway (RTR) is a great way to outsource your closet. I’m upgrading to unlimited next month. Get $30 RTR credit here.

💁🏽‍♀️Dyson Supersonic hairdryer is worth the $400 in time and quality. I give myself professional level blowouts in 4 mins flat.


👀Give me feedback. My goal is to keep in touch with you, update you on what’s happening with me, and add value to you. 

✨Call me out, if you don’t think I’m “being” authentic. Working on being more of me every day because I want to level up. My motivations: to give my fam a good life and to help create a world where tech is created and led by the diversity of our population.

🎙If you hear of speaking gigs on AI + Future of Work, VC, or diversity, send them my way. Whatever I make, I plan to invest in underestimated founders. Read more.


🙏Matt W I appreciate that you cut to the chase, give me constructive feedback, and give me your vote of confidence. Lisa A thanks for crying and laughing with me. Eric N you’re helping me uplevel and I feel it happening. Tom I your sponsorship is noted and you shutting down bullshit when you see it in others is inspiring. Josh T grateful that you support all my shenanigans and are now investing with me in insurtech.  Christy W thanks for being a sponsor and helping me help Baltimore!

✨Lolita Taub
lolitataub.co | twitter | medium

Have comments, questions, tips?  Email me.

🦃 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

🧳 We're not in California

Happy hello! You are receiving Lolita’s Latest newsletter because you are in it, subscribed to it, or are considered a friend, mentor or are family to Lolita Taub. This newsletter goes out every 3 months and includes Lolita’s latest updates, reads, and life hacks. The goal is to stay in touch and share goodies.

We're not in California

Location: Baltimore, Maryland. Josh and Lolita Taub in 110°F weather.

What’s in your dream world? Besides providing a good life for my family, for a long time I’ve dreamt of a world where tech is pioneered by the diversity of its population. For me, that’s meant finding opportunities to promote tech careers and unbiased artificial intelligence, and investing in underrepresented founders/investors. And recently, the universe conspired to allow me to work on almost all of those things in two roles: 1) as chief of staff for a workforce data science company that uses AI to identify individuals with the potential to become great programmers, regardless of background and 2) as a venture partner at a network-driven venture firm.

So, Josh and I moved for #1, and #2 organically happened thanks to a friend’s intro on Twitter. So, yeah. We’re not in California anymore.

We moved to Baltimore, Maryland and survived the 110°F heatwave! 🔥Almost melted but didn't.

We’re enjoying this life adventure together and eating plenty of ice-cream. 🍦We only live once, so make it count, right?!


June | RGA Ventures invited me to their Cannes Lions Festival Innovation Exchange as VC-in-residence. I’m grateful for the opportunity to support phenomenal female founders from around the world and all the rosé popsicles.

Location: Cannes, France. RGA Ventures Cannes Innovation Exchange.

June | I celebrated my 15th-year high school reunion in Andover, MA at Phillips Academy. It was nice to see my old friends all grown up. And so excited that one of my besties now lives in DC.

July + Aug | The interwebs welcomed my new chapter in life through a down-and-dirty Crunchbase interview, Technica.ly Baltimore feature, Forbes Q&A and lots of Twitter love. Thank you!


  1. Women | The Moment of Lift: How Empowering Women Changes the World by Melinda Gates. It is a humbling look into the lives of women around the world, the importance of lifting women, and ideas on how to do it.

  2. Simplifying Life | Essentialism: The Disciplined Pursuit of Less by Greg McKeown. This is a great book for anyone who is busy all the time and wants to do something about it.

Life Hacks

  1. Eco-Friendly Sparkling Water | If you love sparkling water and want to reduce your plastic bottle carbon footprint, check out Sodastream. I can’t believe I hadn’t bought one before.

  2. Massages | My neck and shoulders get super tight from spending so much time on my laptop. One thing that’s helped is this inexpensive and effective Costco massager. Check it out.


  1. My sister, current health care volunteer for Peace Corps Ecuador, is coming back to the states this month from and will be looking for a part-time job as she applies to med-programs. Are there any health-tech startups looking for virtual young talent with enterprise tech sales and nutrition/sex-ed training?

  2. Do you know any awesome chief of staffs with whom I should be connecting, or people in general that I should meet in Baltimore?

  3. Update me on you and tell me if I can be of help!

Special Thanks! Josh T for being that person in my life that always says, “Let’s do it!” My mom, brother, and sister for always being there and loving me unconditionally. Suzy R and Eva H for being champions. Matt W for reaching out to your network to introduce me to good people.

Lolita Taub


🎉I landed my next, thanks!

Hi, as many of you know, I have been on a hunt for my next for a bit, and I just found it!


🎉 Found a job at a company that aligns with my life’s purpose and I’m energized by it!

🙏 Grateful for your support. Happy to help you how I can.

💰 Plan to stay involved in venture.

💁‍♀️ And I want to stay in touch.

Long form

For a while now, my life’s purpose has been to give my family the best life I can provide and to push for a tech industry built and led by the diversity of our population. So, I am grateful that I’ve gotten to work on my purpose as an LP for Portfolia’s Enterprise Fund and as a VC with Arlan Hamilton, Christie Pitts, and the rest of the Crew at Backstage Capital, a fund that has invested in over 100 Pre-Seed and Seed tech startups led by diverse founders.

Now, thanks to a fellow VC who introduced me to an opportunity that was too intriguing and aligned with my interests and values 🥁🥁🥁 I get to continue living my life’s purpose as chief of staff at Catalyte, a fast-growing workforce data science company that uses artificial intelligence to identify individuals, regardless of background, who have the innate potential and cognitive ability to be great software developers! It is backed by Steve Case’s Rise of the Rest and Cross Culture Ventures. Bonuses: Catalyte uses AI for good (I’m a fan!), I get to be the right hand to a CEO who is a values-aligned World Economic Forum Young Global Leader with awesome business chops (he grew his previous company to the hundreds of millions in revenue and it was acquired!). And I plan to stay involved in the venture-startup scene. Just think of all the great insight I’ll be able to share about issues faced and approaches taken by CEOs, boardroom dynamics, the future of work, and growing an enterprise...

🎉I’m so excited I wrote a post about Why I'm Joining Catalyte as Chief of Staff on Medium! 🎉

I owe a big thanks to all of you for being my support system - meeting up, getting on calls, asking me tough questions, asking me to dig deeper, giving me constructive feedback, and introducing me to other amazing people. Thank you! Anything you need, if I can help, just reach out.

Ready to get to work (from Baltimore) and stay in touch,

🚗 Road Trips, Transitions, and Family

Happy hello! You are receiving Lolita’s Latest newsletter because you are in it, subscribed to it, or are considered a friend, mentor or are family to Loita Taub. This newsletter goes out every 3 months and includes Lolita’s latest updates, reads, and life hacks. The goal is to stay in touch and share goodies.

Road Trips, Transitions, and Family

Location: Carmel by the Sea. Lolita, Choco, and Josh Taub.

Did you have a good time celebrating the Mexican Army's victory over the French Empire at the Battle of Puebla, on May 5, 1862, this Cinco de Mayo? Like good Mexicans, Josh, Choco, and I did not celebrate. We did go on a fun road trip to the Bay, though! We saw wild zebras 🦓near Hearst castle and elephant seals in San Simeon.

So, why the Bay? It’s all for the dream to learn from the best, and invest in and support the diverse founders who are building the future of tech. And with Backstage shifting its focus to an accelerator model and my mentors pointing me in the direction of the Bay, it was the right time to come out. So, I’m here - looking for the right fit fund.

Ideally, I get to work with a B2B enterprise-focused seed fund that’s in the $50-100M range that appreciates diversity and is committed to the development of - not only the portfolio companies but also - the team. You can read more in my All Raise #WCW Enterprise Feature here (thank you ✨Sharvari!).

🚨Until I find the right fund and role, I plan to take on consulting gigs with young and diverse pre-seed and seed funds working on ops (e.g., collaboration wikis, CRM) and investment team projects (e.g., deal flow strategy, due diligence structure).

I’m excited about what’s to come and grateful that I get to enjoy a bit more time with family!


Mentee | My All Raise VC Champions mentor, Mark Suster, Partner at Upfront Ventures and author of the renowned blog Both Sides of the Table, shared these words with me. They shifting my thinking and might shift yours too.

Writing | Blogged about alternatives to VC funding, VC fundraising prep, CVCs, and M&A on Medium. Posted my 2019 AI Market Review on Slideshare.

Community | Held Backstage Office Hours at SaaStr and SXSW. Mentored the Techstars Anywhere Cohort and judged the Startup of the Year Pitch Competition. Took on a volunteer role at All Raise as Co-Lead for the Intersectional Working Group and participated in First Republic Bank’s Women In Venture Summit.

Transition | Started my job hunt with this tweet storm (it’s earned 33.6K impressions)! Here are my current stats: 33 leads (21 inbounds). 9 turned out to be duds. I passed on 5 funds and 5 funds passed on me. I have 5 qualified opportunities and 9 leads that need to be qualified. Fingers crossed.

Health | Got bed bugs in my first apartment in SF. That took me out for a bit. I’m recovered, now, armed with a bed bug detector from Amazon, and back on the job hunt. Grateful for good health!


May is #mentalhealth month. So, I’m sharing some of my favorites on the topic.

Dyslexia | The Dyslexic Advantage: good for those who are dyslexic (like me) and are curious about the superpowers that come with dyslexia. This book is written by two physicians.

Workaholism | Chained to the Desk + #Chill: good for those of us who work too much and want to learn to chill. This book is written by a recovered workaholic + psychotherapist.

Self-Help | What I Know for Sure: good for anyone who has gone through some tough stuff and wants to be uplifted. This book is written by the soulful billionaire Oprah Winfrey.


Bed Bugs | Detect bed bugs before they bite you. I got this detector and plan to use it forever.

Introverts | I’m an introvert and don’t often find social channels that delight me. So, I was happy to find Marzi’s @introvertdoodles on Instagram. Check out her posts. They just might just make you smile and nod.

Sinuses | My sinuses flare up when I travel and sleep in too dry a room. This month, I started using this mini travel humidifier and my sinuses are much happier.

Rewards | A better service needs to be created for managing rewards (so they don’t expire before you use them). The best one I’ve found is AwardWallet.


Intros | Is there anyone with whom you would recommend I connect - for consulting gigs, fund roles, or just because he/she is awesome?

Parent | Do you know a good person who can provide advice on taking care of a parent who is not yet in retirement age, has no insurance and may become disabled?

You | Tell me what you’re up to and how I can be of help to you!


Josh T for being my rock and being the best partner anyone could ever have in life. Christie P and Arlan H for your warmth, care, and job hunt support. Mark S for your mentorship and documentary and book recommendation. Charles H for your mentorship and intros. Suzy R for being a friend and introducing me to an awesome AI company. John O for your mentorship, inside scoop, and friendship. Al G for opening up your network to me! Nnamdi O and Aaron H for your job hunt support! Nick N for going above and beyond for me. Kevin B and Karim C for the awesome cap table waterfall session + model. Kim P for sharing what you’ve learned over the years in the business. Navrina for constructive feedback and intros. Ryan K for the invitation to be a mentor at Techstars Anywhere and for your candid feedback. Bryan L for peer editing my posts. Hana Y for the invite to First Banks women in venture summit. Aileen L for entrusting me with the intersectional working group co-lead volunteer role at All Raise. Sharvari J for the AR #WCW series feature. Matt W for being you. Todd K for snail-mailing over your Built for Change and Steve C’s The Third Wave book. Al G, Adina T, Evan M, Michelle M, and Greg S thanks for being allies.

I am so grateful for all of you.

Lolita Taub


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