Secretly Building a Company While At Your Day Job: A One-on-One Interview With An Incognito Entrepreneur

I have multiple identities. During the day, I attend school and class and listen to professors and write papers. During the nights and weekends, I interview people about their journeys in HR. I’ve been learning about how to juggle multiple identities, but I have finally met the master.

Her name is Jennifer Fish (not her real name) and she’s a master at management. During the day, she manages people as a VP of Product. During the night, she is managing a dream: a workplace where women are given the same equality as men in the workplace.

And she’s totally normal, kinda like me.

When I sat down to speak to Jennifer, I knew that she works for a software company as the VP of Product after a career in Product Management in the tech industry. I quickly learned that Jennifer is currently living out of the country and was speaking with me at 11 PM her time. Talk about dedication! 

I also found out that Jennifer is embarking on an incredible journey alongside her day job: she is building a company, designing a fair trade label for inclusivity and equality in the workplace. Jennifer is creating a format to consult companies for their efforts of equal pay, inclusive practices, hiring,and promoting and to offer them a label to put on their products or services recognizing their efforts. This, in turn, offers a huge revenue potential for companies. 

Yeah, my jaw fell open in admiration as well.

I am very impressed with Jennifer, and I wanted to know more about both her 9-5 and her side hustle. What is it like to be the VP of Product at a company, and being the person that everyone comes to for answers? How has this management changed as she has set off to start her own business, and has started to manage herself? And on the flip side, how does she simultaneously manage herself at her solopreneurship? 

Let’s start off with Jennifer’s managerial role as the VP of Product. 

Managing people seems like an ability that feels effortless and natural. Whenever I have thought about becoming a manager in the past, I always thought I could easily fall into it, and that with the right company and team, it would be simple to help employees with anything they’re confused about. 

Looking back at this thought, I see how that was a little ridiculous. After taking one Business class in college, too, I really learned how managing people and taking on other people’s projects as well as my own is a skilled task that takes experience and talent. 

And from what I can see, Jennifer has that talent. Having worked in Product Management for over 10 years, Jennifer has a long line of experience working with people on teams and working out the kinks of any given project. And in her work now, she is the one who leads these teams to make sure the product conveys what the CEO wants, and develops the strategies to make the product as best it can be.

I asked Jennifer what it means to be a manager for many people, and the responsibilities that come along with the role. Jennifer had two main points to say about her managerial and leadership work:

1. Much of the job is coaching and cheerleading her employees. Jennifer is at the top of the product team, and is building the strategy for how the product will develop and grow. However, she is also the go-to person for the details along the way, if anyone on the product management team has a question about the vision and implementation. 

Not only does Jennifer have to understand the quality of the product and the technique of the work, but how to communicate with her employees to make sure they understand as well. That takes an entirely different skill set than the hard, technical skills that is required when building software. Leadership and management are built on the soft skills - effective communication, encouragement, time management, validation, and pointing people in the right direction while remaining thankful for employees' hard work.

2. Managing is never the same on any given day. When working with employees, you are not only working with the actual work they do on a daily basis, but their emotions, habits, and the backstory of what might be going on in their lives outside of the office. Deadlines may come in late, or a difficulty in the technical system may act up, which will need to be addressed by Jennifer. While Jennifer has a team of other managers, as well as the employees on the product team, what she will be doing everyday changes constantly. 

Managing requires the duality of being really good at the job you were hired to do, and being really good at helping your employees produce the product that the CEO of the company believes in. You have to be communicative, respectful, and enjoyable, while getting the job done. Jennifer seems to be performing this duality skillfully.

So we know that Jennifer is an amazing manager for others. But how does Jennifer transfer these skills as a manager of HERSELF at her own company? 

What is that transition like to go from managing other people, to managing yourself for your own company’s growth? (While also doing it simultaneously)?

I am very interested in learning more about the entrepreneur experience. I have never had the urge to pave my own path and do something because I wanted to, but I see those who do and stare at them in awe. Luckily, I’m interning with an entrepreneur (shoutout Dan), and I get to see the motivation and belief in a company grow into something real and exciting. I was even more lucky to get to interview Jennifer, who is building a fantastic business and product as we speak. I was curious to know how she does it all, and what the main differences were between her day job and her entrepreneurial endeavors. 

Jennifer laughed, and told me the clear differences, but also the key similarities between the two roles:

1. Normally, when developing something new and testing out the capabilities of its production, there are other people around you. There is usually a team of people testing different markets, asking opinions from other people, and adding their two cents into the implementation. In the early stages of an entrepreneurial product, however, all of that is done by yourself, says Jennifer. Jennifer has identified a problem and has developed a hypothesis of how to fix this problem, and it is now up to her to do all of the usual market testing techniques, without a set team behind her yet.

Jennifer has taken to LinkedIn and her network to find those opinions and markets to test her company’s idea. When she told me that she was building a universal label to establish a standard for gender equality in the workplace, I literally said out loud, “That is a genius idea.” While my comment may not have been the most helpful in testing her product out, having conversations with anyone she can reach out to on LinkedIn or other social platforms who can offer feedback elevates the entrepreneurial capacity for success.

2. There’s more work to do, but you can go in whatever direction you want to. Jennifer, as a product manager, is holding her team accountable to do the work, but ultimately, it is up to the CEO of the company to decide the direction the business will go, even with input from the team leaders. Now that Jennifer is developing her own product and business, the work she puts into it can be a lot at times (especially while also working a full-time job), but if she wants to change the direction of the company or the label, she can in a heartbeat. This work demands major organizational skills too - which you can learn how to juggle in my on-demand organization webinar course, coming out the week of April 26th.

Jennifer gets to decide for herself, do I like how this is going? Do I like how I’m managing myself to get it all done? Those are the questions she only has to ask herself, not anyone else. That feeling must be freeing, if not nerve-wracking sometimes.

As Jennifer is learning and growing as an entrepreneur, she’s finding the tricks and tips to lead herself successfully. In her words, she’s scrappy, finding time in between meetings and mornings of her full time job to put the product work in. She is finding every possible way to get feedback on her product, and is organized to the max in organizing those conversations.

If I ever become a manager one day, at a 9-5 company or in my own entrepreneurship, I will think back on my conversation with Jennifer. She showed me what it takes to be a leader, not just in a particular position doing the technical role, but helping others achieve their goals simultaneously. I also learned from Jennifer (and my supervisor, Dan) that taking the risk to add multiple identities into my work, in order to do something different and self-created is doable, and feels extremely rewarding with hard work. My multiple identities do not have to leave once I graduate college, and as Jennifer has shown me, focusing myself on different passions can make up my whole. 

I hope to see Jennifer’s product stamped on all equal paying, equal hiring companies in the future, and I can’t wait to see how Jennifer’s fabulous leading skills will lead her to long-term success.

Note: Some of the names have been changed to protect confidentiality.