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The Entrepreneur Paradox

The Entrepreneur Paradox: Why Startups Care About Your Side Hustle

For the month of July, Jackrabbit is partnering with Austin Digital Jobsone of the largest networks of Austin professionals with 30K members – to share our insights on landing a job in the Austin startup community. This 4-part series is called Why Austin Tech Startups Aren’t Hiring You: Counter-Intuitive Insights to Land Your Next Job and can be found on our blog or by subscribing to ADJ’s TGIF newsletter – a thoughtfully curated list of links relevant to job seekers, career refiners, and hiring folks alike. 

The Entrepreneur Paradox is the first blog post in this series.

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While some job seekers may feel the need to hide or downplay their side ventures, we believe your side hustle actually makes you more hireable – especially in a startup environment. (A side venture can be a small “project” that generates money, or has the potential to, or an actual business that you run part-time.) Whether it’s selling art at vendor events or coding a personal finance tool, here are 3 reasons why your side hustle can actually be an asset and how to frame it to future employers. 

1. Side hustles demonstrate that you’re a T-shaped person.

A T-shaped person is an individual who possesses deep expertise in one area (vertical bar of T) with generalist knowledge in other areas (horizontal bar of T). If you’re running a small business or have a “side project,” you most likely have above average (if not expert) knowledge in your domain, as well the passion to pursue something outside of normal work hours.

In addition to specialized knowledge, you’ve probably also dabbled in the minute details of running a venture – from hard skills such as marketing and finance to soft skills like staying organized with project management tools and talking to customers.

This diversity of skillsets makes you an awesome candidate for a startup.

The reason that T-shaped people are highly valued in startup environments is obvious. In small teams that are highly interdisciplinary and cross-functional (for example, Jackrabbit is about 20 people), individuals not only have more responsibilities but also more diverse tasks thrown at them.

Startup teams consider each person the resident expert in their domain who also has the ability to flex in other areas as the company’s needs and priorities fluctuate over time, possibly even on a week-to-week basis. To use an overused cliché, everyone wears multiple hats.

Here’s an example of how you can frame your T-shapeness to a potential employer. Alex Mitchell, our project manager and jack-of-all-trade, also runs a company outside of Jackrabbit called Music Meets Video. Here’s how he speaks to his experience.

“When I framed my experience at MMV to Jackrabbit, I talked about the learning process of starting a company without any prior knowledge of how one goes about doing that. Everything from writing a business plan, building a product, working with a development agency, hiring interns, and a hundred other things – it was all brand new to me. I wanted Jackrabbit to know that I was a utility player and could accomplish anything they asked me to do because I have the drive and motivation to do good work. Today, I find myself consistently adding value to the company via skills I’ve picked up through my startup experience. As a bonus, I now get to serve as a trusted advisor to clients who are starting their own businesses for the first time.”

2. Side hustles show that you share common cultural mindsets.  

When hiring a new team member, companies, especially smaller startups, care about a good culture fit. “Culture” is a vague word that gets thrown around a lot these days and is often conflated to mean ping pong tables, catered lunches, and beers on tap. At Jackrabbit, we believe those things are “perks” not “culture.” We define culture as the interplay of relationships, the environment (including psychological safety), and the mindsets of an organization.

For us, a side hustle is one of the best indicators of (and tangible argument for) how well an individual will thrive in our entrepreneurial, self-driven culture.

If someone is already pursuing a venture outside of work, they probably share our two key mindsets: a beginner’s mind (an attitude of openness and curiosity, eagerness to learn, and willingness to try) and a scientific approach to problem solving (running experiments and reframing failure as data points).

As an example, I (Nina Ho) lead marketing and business development here at Jackrabbit. In my spare time, I run a company called collective blue. We help diverse creators, such as women and people of color, get their work out into the world and get paid fairly through products, digital storytelling, and events. How I would frame my side venture as related to shared cultural mindsets would be something along the lines of…

“In starting collective blue, I had no idea if the concept would catch on or not, but I knew I had to try since the lack of diversity in the Austin creative community is a problem I’m passionate about solving. Running a double-bottom line company (people and profit) has taught me to be flexible in pivoting when experimenting with new solutions to generate revenue. In a fluid environment such as a services startup like Jackrabbit, I believe my willingness to try and my ability to be flexible when challenges arise will serve the team well.”

3. Side hustles shows that you’re, obviously, a hustler.

In the words of the venerable and timeless Mary J. Blige…

“See I got my mind right, I’m a stay on the grind / I’m a put my work in / Get in where I fit in (Cause I hustle!) / Seven days of the week (I hustle!) / Just to stay on my feet.”

A hustler is someone who shows up, has a strong work ethic, and does what needs to get done in order to achieve an end goal. 

Hustlers don’t need to be grinding “seven days of the week” but should be able to step up when a challenge arises – such as a client fire or unexpected deadline. Startup environments are by nature fraught with uncertainty and change, both good and bad, and having employees who can put their heads down and do what needs to get done is extremely valuable. This is especially true if you’re speaking to or interviewing with one of the co-founders. The company is probably their “baby,” and founders want to trust their employees to make tough decisions and deliver under pressure when the situation demands it.

Note: Hustling should be sprint-based not a marathon. Be wary of companies with cultures that valorize overworking oneself – veiled as “being super passionate” – over self-care.

An example of a hustler at Jackrabbit is Brendan Kelly, our other project manager here at Jackrabbit. In addition to helping clients build products at Jackrabbit, he also works as a freelance process consultant, helping teams implement Agile software development practices to more efficiently build software.

How Brendan could frame his hustling ability to a potential employer would be…

“There’s a lot of flux and change in a startup environment that requires quick thinking and execution. I love working in this kind of environment because I like making tough decisions and having to execute under pressure. Freelancing taught me how to deliver when the pressure is on. Just the other week, I had to turn around a huge deliverable in just 2 days with the whole contract on the line. I’ve been in this kind of situation many times before, which helped me stay calm and deliver within the tight timeline.”

Key Takeaways

As a job seeker looking to work at a startup, you could be putting yourself at a disadvantage by not speaking up about your side projects. Side ventures demonstrate that you have a diverse skillset, share common perspectives of looking at the world and conducting business, and can hustle when the situation arises.

As a caveat, it’s not cool to have an about-to-launch-and-I’m-going-to-quit-almost-immediately venture and not communicate that to a potential employer. This is especially true for smaller startups which are very intentional about resourcing (as they should be). There’s nothing wrong with earning money or building a runway in the interim of your company’s launch, but don’t accept a full-time offer only to bail a month or two down the road. Depending on the company, there may be opportunities for part-time or full-time contract work that could be a win-win for both parties involved.

Lastly, this advice is geared towards startups, especially those with under 30-ish employees. Large corporations may still be wary of entrepreneurial pursuits outside of work. Even so, that assumption is changing as corporations are trying more and more to encourage “intrapreneurship” – driving innovation within a large organization.

Stay tuned for more of our 4-part blog series on Why Austin Tech Startups Aren’t Hiring You: Counter-Intuitive Insights to Land Your Next Job. Next week’s topic is Part-Time Isn’t Right All The Time – why defaulting your job search to “full-time” and ignoring “part-time” or “contractor” opportunities could be hurting your career. 

At Jackrabbit, we’re always looking to work with awesome people and are flexible with our work structure (full-time, part-time, contractor, etc.). Shoot us an email and say hi at We’d love to hear from you.

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Author: Nina Ho heads marketing and business development at Jackrabbit. When she’s not wearing all of the hats, Nina enjoys playing basketball, running collective blue, cooking Vietnamese and Thai food, and breaking it down on the dance floor.

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