Who's the Boss? with Upside Member Lindsay Tabas

In the Fall of ’02, Lindsay designed her first user interface while studying engineering at the University of Virginia. Since then, she has been passionate about designing technology for people. Under the name Lady Engineer™, Lindsay offers her clients a unique program that combines 1:1 coaching, startup focused scripts, templates and guides, and an exclusive support community with their peers.

What did you do in your past life before going out on your own?

Prior to launching my consulting business, I worked exclusively in the technology industry, first on enterprise software, then in startups. I started my career in the Bay Area with a twinkle in my eye to make it big in the startup scene. Over my career, I have worked sitting in between the customer, the engineer and the investor. With my engineering degree, I combined all that I know into a systematic process for getting founders up, running and sailing with confidence.

What's your current elevator pitch?

I help early-stage tech startup founders prove their market and revenue model so they sell the right product before spending a lot of money building the wrong one.

How long have you been working as a consultant?

Since Jan 2014.

What made you decide to go out on your own?

In 2013 I started an e-commerce boutique while working at a startup. Heading into 2014, I decided to find a full-time job at a slower paced and less demanding company. The plan was to test out a lot of my hard-won startup lessons in a “sandbox” with littler personal risk.

After 6 weeks, there was a major foil in my plan: The temp-to-permanent contract I took at this new company did not turn into a full-time job. I was without a job and had no idea when my next paycheck would come and from where. This was scary! Don’t get me wrong, I was panicking. I had not financially prepared to be out on my own.

In one week, putting some of my skills and tactics to work, I got a new contract making twice as much per hour for the next 3 months. Literally, I was unemployed for only 1 week. “So this is what entrepreneurship is like?” It was exhilarating.

What has been your biggest *win* as a consultant?

It’s important for me to not to sugarcoat things for others: the biggest *win* is that I’ve been standing on my own two feet as an entrepreneur for four years and counting. As far as work goes, I’d say doing consulting work for a Fortune 50 company while also coaching an entire cohort of Techstars’ startups made me even stop and pause: Wow.

What has been your biggest challenge as a consultant?

I know that Lauren Cracower said that “doing it all” is a big challenge, and I definitely agree; it’s not easy to learn to manage a business and manage yourself as a business. For me, the biggest challenge has been riding the emotional rollercoaster with finances and shaping a business model that I could truly scale as a consultant. It’s incredibly scary and empowering to not know where your next paycheck is coming from.

What was your biggest stumble and what did you learn from it?

In my first two years, I rode the wave, taking opportunities when and where they appeared. It’s really easy to do that in a city like New York; there are companies that will hire you for 3 weeks, 6 weeks, 3 months, etc. When I moved to Philadelphia, those opportunities don’t exist. So for year 3, my word was “focus” and it was powerful. I focused on managing myself, managing my business & managing myself as a business. When I really dialed into productivity and focused goal setting, I realized little strategy I had the first 2 years.

What do you love most about being a consultant?

Bar none, the freedom and flexibility. I don’t have to ask anyone permission to take the afternoon off to see my dentist. I can start working first thing in the morning without commuting an hour to sit at a desk. I can control when and who I meet with so I can use my most productive hours to do the work I need all my brain cells to do.

How did you land your first client?

As I mentioned before, my first “contract” was a position I thought would go full-time. That came through a recruiter. The second also came through a recruiter that works in my space. I had built a relationship with her over the years so she was the first person I called.

The next two big projects, one for the Fortune 50 and the other for Techstars, came through my network. For the Fortune 50 company, I was referred by a coworker from IBM Research in 2006! It was crazy to me that 8 years later he thought of me. The Techstars project came through a younger woman I had mentored the previous year.

What steps do you think professionals should take when first starting a consulting career of their own?

If I could turn back the dial, I would say this: One, it’s great to start your journey into entrepreneurship as a consultant because it requires the least amount of startup costs. You’re selling your skills.

Two, build a network of peers and advisors that are anywhere from a few months to years or decades ahead of you as independent consultants. You’re going to need to lean on them when you have questions along the way.

Three, think through the ways that you’re going to get clients, the skills that you’re going to offer, the people you want to work with, and how you’re going to operate yourself each day. Like anything, those daily, consistent exercises and habits are what lead you to success.

Who helped you along the way and how did they help?

I could not have done anything in this space if it were not for my parents, both of whom are self-employed. Many entrepreneurs get the “I’m scared for you” looks from their friends and family. Not me! My Mom, Linda ( has had her beautiful gift shop since the 1970s and my Dad Jon has been an independent civil engineer and land surveyor since the early 1980s. They both understand the struggle but also the unending desire to manifest our own destiny. Most importantly, there’s a lot of teamwork just within the family.

What do you think is the biggest misconception about consultants and freelancers?

I think a lot of people on the sidelines see it as a lot harder than it can be. Some independent contractors move from 1 year contracts to the next, taking off a few weeks or months in between. Others have solid relationships with a handful of larger consulting firms so they’re being tapped for a variety of short term projects all the time. Obviously, there are others like myself that have a specific mission and specific tastes in projects and clients; that makes working on your own a lot harder.

What advice would you give someone who's interested in going out on their own?

To build on my previous answer, I would tell this someone that if they know their risk tolerance level, they can design their ideal entry into the consulting game. There are options for those of you that are risk tolerant and those of you that are risk averse.

Where do you see yourself in 10 years?

What's next for you?

My mission is to increase the success rate of people-minded technology entrepreneurs so that we can all design ourselves into the future. We’re at a pivotal moment where we, as a society, need to decide if we want to use technology or technology is going to use us. In the next ten years, I want to reach 20 million people, be an active speaker, have a TV show, help design academic curriculums and fund my own innovation lab.

Any other tidbits you'd like to add?

I offer free 45-minute strategy sessions for any startup founders that are building some technology as part of their business. Please find my calendar here:

Lindsay Tabas is a member of The Upside and founder of the Lady Engineer™. Through her 15 year career, Lindsay has worked with over 100 startups and investors, as well as teams across Fortune 500 firms. She speaks two languages: the subjective ways of people and the objective thinking of engineers. Her education is in human-computer interaction, her profession is digital product development, and her persistent passion will always be to design technology for people. See some of Lindsay's case studies here:

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