Allison Esposito Medina is the founder of Tech Ladies, the largest community of women in tech. Since launching it in 2015, Allison has grown the community to over 200,000 members and millions in revenue, before it was acquired last year. Since the acquisition, Allison is now an advisor to Tech Ladies, and has launched Bootstrap to Millions, a newsletter to help folks build profitable businesses without venture capital.
Can you tell us about your background, including where you grew up, your family, what you wanted to become when you were a child, and your career before becoming an entrepreneur?
I grew up in Westchester, NY right outside of New York City, in a big, loud Italian family full of musicians. When I was a kid, I always wanted to be an entrepreneur, I just didn’t know it yet. I had a successful lemonade stand. I sold gift wrap door-to-door, I picked weeds for my neighbor, all before the age of 14. Then I got my working papers on my 14th birthday, not a minute later. I was just always fascinated with making and managing money.
How did the idea for Tech Ladies come about, and what was your vision for the community when you first started it?
I started Tech Ladies because I was working in tech and wanted a way to build my own network and help others find jobs. Then it continued to grow because there were SO many women in tech who felt the same. My vision was to grow it as big as possible, but I never dreamed it would also have so much impact, so many people have found jobs on Tech Ladies, negotiated raises with the help of our career coaches and community, and so much more.
How have you grown Tech Ladies into a community of over 200,000 members, and what are some of the most effective acquisition channels you've used?
The most important thing we did for acquisition was create repeating ways for folks to interact with Tech Ladies. So one event per week, a weekly job drop email, that kind of thing. The more repeating ways to provide value to folks, the more they will get to know you and what you provide. This is kind of an underrated way to grow, because it requires you to stay focused, have a plan, and just execute on the same thing over and over, and not get distracted by all the shiny new projects that you could be doing.
What do you consider to be the key factors that have contributed to Tech Ladies' success to date?
Our community and our team, for sure. The community gives so much to each other both at events, in the online community and even in person when they decide to meet up. I am always surprised at how generous people can be with each other when organizing around a common problem. Also, our team is world class. They are now running Tech Ladies without me since the acquisition last year, and I couldn’t be more proud of them.
What were some of the biggest challenges you faced while building Tech Ladies, and how did you overcome them?
Lack of capital meant that we built bootstrapped. We were able to generate millions in revenue even without having raised any money from investors, so now I am passionate about teaching others how to do the same. I launched Bootstrap to Millions, a free newsletter, to share more of this, and I’m writing a book about it!
What can readers expect from the newsletter?
In the years since I have been building, the numbers for women and underrepresented founders who get venture capital funding basically hasn’t budged. It’s still around 2%. Does that mean every woman who wants to build a company should just forget about it? NO! Venture capital is a great tool for those who can access it, and for the right kind of companies, but for everyone else – the other 98% – we need options that teach us how to build. I’ve learned so much in my 8 years building a bootstrapped, profitable startup, that I want to share it with others. The newsletter is a mix of my writings and resources/links that will help anyone who is building or wants to build a business.
How have you seen the tech industry evolve in terms of diversity and inclusion since starting Tech Ladies, and what do you think still needs to be done to promote greater equality?
It has barely gotten better in the 8 years I was working in it, to be honest. I think our collective culture has to some degree started to believe women a little bit more about their lived experiences, but it’s going to take a long time to turn around the sexism that is rampant in this industry. The best thing companies can do is continue to hire women, fund women and promote women on their teams.
What advice do you have for women founders who are just starting their own businesses, and what do you think are the most important qualities for success in entrepreneurship?
Stay focused on your customers or community members. If you stay close to what they want and need, you can continue to build valuable products and services for them. It’s not about you. Get comfortable with the exhaustion that comes from making high level decisions but then also answering customer service emails. You’ll need to context switch between the macro and micro for a long time, so the sooner you accept that the better!
Get good at firing yourself, over and over. You’ll do everything alone at first then eventually hire for it. When you do hire for it, trust the people you hire to do it their way, and back off. Monitor and only step back in if it isn’t working.
Question from the community: Could you share your insights on how to effectively collaborate with other businesses, where to start, and how to ensure mutual benefits in such partnerships?
Yes! Make sure the partnerships you’re pitching are equally valuable to both parties, make sure the offer is balanced. For example if you want to swap a newsletter feature with another company, and one of you has a way larger list, offer to segment the list so it’s a fair swap. And make sure to balance out which team is doing most of the work. The more you do partnerships, the more you’ll find out what is and isn’t worth your time.
What are your goals for 2023?
I’m on sabbatical after almost 8 years of building a company! Other than working on Bootstrap to Millions part-time, I’m an advisor for Tech Ladies, I’m angel investing, training a rescue puppy from scratch and trying to enjoy my life a little before I go out and build something else!
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