⚡️ It's my Day One. It can be yours too.
Join me on my journey as Lex CEO. Read my three key lessons so far.
HI MY NEW READERS 🙂 I’M SO HAPPY YOU’RE HERE.
👋🏻 I’m Jenn, today is day one as my official first day as a CEO of Lex. The LGBTQ+ app for queer community. I’m starting this substack to document my learnings, wins and losses as I build this business. All the juicy messy BTS tidbits you don’t see in the PR. With less than 1% of VC money going to LGBTQ+ founders and less than 2% to women founders, I want to shine a light on the inside process of VC through a human lens. I’m here thanks to my amazing business partner, friend and Founder of Lex - Kel Rakowski, as well as the team at Lex and our investor supporters.
📖 LET’S START WITH STORY TIME!
Let me introduce Lex
🔥 The story of Lex starts with like with all good stories, a women-run erotica magazine of the ‘80s and ‘90s On Our Backs. In 2017, Kel Rakowski asked for followers of her Instagram @h_e_r_s_t_o_r_y to write their own personal ads. The app was crowd-funded with $47K in Kickstarter support and fundraising parties. It was an instant hit with hundreds of submissions each month. In the summer of 2020 Lex raised $1.5M led by Female Founders Fund.
[Subscribe for more on the history of Lex in a future post]
And here’s my backstory to Lex
🏳️🌈 My story to Lex starts with me surreptitiously eavesdropping on Kel at a co-working space called the Wing in 2019 (RIP). She was with who I now know to be her girlfriend talking about her plan to find the money to make Lex happen. I was 32, just coming to terms my own queerness and reeling from the aftermath of a painful divorce as a result. In essence, I was a hot mess, but my ear for gay related topics was on point!
[Subscribe for more on my hot mess stage(!) in a future post]
☕️ I was not brave enough to interrupt her but I knew of Lex (then called Personals) from the Instagram - so in a bold move I decided to get in Kel’s DMs and propositioned her. At the time I was running my own consultancy for early stage start ups - helping them with marketing, growth, strategy and investor fundraising. I wanted to help. Prior to my gay awakening and very first girlfriend at 31, I had never explored queer culture. I was ready to make up for it and use what I did know (business) and apply it to supporting others in this community. I didn’t want other people to have to wait as long as I did to embrace their full spectrum of self and find people to share that with. I said I wanted to help and would be in the co-working space later that week if she wanted to meet for coffee.
[Subscribe for my tips on making that cold outreach in a future post]
🤖 The rest as they say is history. I started coaching Kel for her first fundraise - working on the deck and building excel spreadsheets. We’d meet and chat through the highs and lows of starting a business. I was drawn to Kel’s wonderful ability to admit what she didn’t know and have absolute faith in her ability to learn it. Humility is a rare trait in entrepreneurship!
📈 I went to be Head of Growth at Tia - a women’s healthcare company who had just raised a Series A. In the meantime I officially became an Advisor to the team at Lex - meeting their marketing manager weekly to support the teams growth efforts. During that time Kel and our friendship grew slowly, always with Lex as our shared ground. When she closed her Seed round in late 2021 - this time it was her turn to proposition me - did I want to come on full time and be her COO.
[Subscribe for my lessons from scaling Tia from Series A to Series B]
🤨 At first I doubted myself - I was an experienced Growth Marketer, not an Operator, could I do it? Was I qualified? Was I gay enough? But as we talked I realized that Kel saw in me what I couldn’t - I had learnt so much scaling teams at Tia and previous roles - I was ready to lead. We closed the deal over coffee in Golda in Bedstuy.
[Subscribe for thoughts about ‘being gay enough’ in a future post]
🥹 A year later on a slack huddle about something entirely unrelated Kel surprised me once again - blurting out that she wanted to make me Co-Founder. She wrote me the most beautiful letter about the role I had played to date and how she wanted to celebrate that and make me her official partner. She called out the pivotal role I had played in our fundraise and how she knew she needed me to be by her side for what was next. I was so taken aback - and touched. After a heavy dose of emotions - I of course said yes. I just felt so grateful to have a work partner who celebrated my value the way Kel did.
[Subscribe for co-founder lessons from Kel’s & I’s relationship in a future post]
🥾 Cut to a few months ago, while on a walk in Colorado, at a Founders retreat with Slauson our wonderful investors, Kel shared what was on her mind. With her in the role of CEO she felt corned in and that her ability to think creatively and think outside the box (the very type of thinking that had birthed Lex) was becoming squashed. This was taking a toll on her mental health and she wanted to find a way to restore herself back to the creative spark that had started this journey in the first place.
[Subscribe for to read more about protecting creativity in a future post]
🌸 As ever - I was in awe of Kel’s vulnerability and rawness. I listened and made space. We discussed ways to support Kel. I knew that for Lex to thrive, I needed Kel to be the most Kel - creative, curious, unconventional, effortlessly quirky without even trying. This was the magic that has started Lex and this was the fire we needed to keep burning. And in the weeks that followed we came to a new reality - Kel would become Chief Creative Officer (keeping Lex Lex) and I would become Chief Executive Officer (taking care of the business). We built a plan, shared it with our team, investors and press. To us it felt like a big deal, but to every one who knew us, it was the obvious move. We were both playing to our superpowers.
[Subscribe for more on playing to your super powers in a future post]
👩🏼💼 This time I didn’t doubt myself. Kel’s relentless trust in me through this process meant I was now able to place that in myself. So here I am today - ready to step forward into this new phase! I’m honored to be building Lex and realizing our vision of creating a thriving social platform for LGBTQ+ people.
[Subscribe for more on Lex’s vision in a future post]
My lessons from my day one as QCEO:
📲 01. MAKE THE CONNECTION
Send the DM, the email, interrupt the person at coffee - be brave and make the connection. You have no idea where it could lead. If a tiny tiny voice in your head has an idea to do it - listen! The worst that could happen? Absolutely nothing comes from it. The best? It changes your life.
🏅02. THE STRONGEST RELATIONSHIPS CELEBRATE EACH OTHER
I’m so grateful for the relationship I have with Kel. We both deeply trust each other and I feel so seen and celebrated. I know she always has my back and I will always have hers. This means whenever we have conflict we can both be unafraid to say whats up as we know we’re on the same team. I admire her fiercely and am here forever as her number one fan.
🤗 03. YOU ARE ENOUGH
You are gay enough, you are smart enough, you are experienced enough. Whatever self doubt you have - thank it for being there and step forward into the role your life is presenting to you. If there is an opportunity in front of you, it’s there because you created it.
Ask yourself, what or who am I not connecting to because of a fear I’m not enough?
Then consider - who in your life truly celebrates you? How can you see yourself though their eyes and use that confidence to step forward through your fear.
Take the leap. Let me know how it goes. It’s my day one. How can it be yours too?
MY PROMISE TO YOU DEAR READER IS:
I will write honestly and truthfully.
Protecting my team is my upmost priority. Anything referencing specific people has their explicit permission.
Im committed to learning - I welcome feedback, good, bad and the rest. You can reach me jennifer@lex.lgbt
Love this! Such an exciting time at Lex! I've been following along their journey since the @h_e_r_s_t_o_r_y Instagram days and have loved following along their journey both as a queer person and a person in tech. I found your substack on LinkedIn which I love because usually I don't find anything this personal or real on there so this was a cool find. Can't wait to keep reading!