Lift Your Legacy: How being a busy mom launched my entrepreneurial journey with Jugl CEO Amy Rosenow and Rabbi Jacob Rupp

There is no “fitting life into your business/career” as I see it. Life is what we live every day, whether we are at work, on a glamorous vacation or home, sick. It’s harder than it used to be because the rigid line between life “at” work and “outside” of work has dissolved for most knowledge […]

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There is no “fitting life into your business/career” as I see it. Life is what we live every day, whether we are at work, on a glamorous vacation or home, sick. It’s harder than it used to be because the rigid line between life “at” work and “outside” of work has dissolved for most knowledge workers.

Amy Rosenow is an entrepreneur, financial industry veteran, hedge fund and angel investor, passionate working mom, and philanthropist. She is CEO and Founder of Jugl LLC, a software company focused on making it easier to be a working parent.

Prior to founding Jugl, Amy served as Chief Operating Officer and Chief Compliance Officer of Sheffield Asset Management (a Chicago-based investment manager), for over a decade. She began her career on Wall Street, working for Morgan Stanley, JP Morgan and Bear Stearns.

Amy graduated from Cornell University. She lives in Chicago with her husband, two daughters and their chocolate Labrador retriever.

Thank you so much for doing this with us! What is your “backstory”?

Jugl is the passion project of a working mom. As Chief Operating Officer and Chief Compliance Officer of a hedge fund for over a decade — along with having a husband, two kids, and a dog − there were always so many balls in the air! I had an epiphany: it was almost as hard to be COO of our household as it was to be COO of a billion-dollar investment management company!

My husband is a brain surgeon (literally), so in our crazy house, my COO job was the “flexible” one. I constantly tried out new tech and processes to make our lives run more smoothly, but the existing technology just wasn’t good enough. I knew there had to be a better way to manage the information and logistics of busy modern families, so I decided to create one! And so began my entrepreneurial adventure! I joined 1871 (Chicago’s technology and entrepreneurship hub) and was soon off and running in this exciting (and sometimes scary) Jugl journey.

Can you share the funniest or most interesting story that happened to you since you began leading your company?

One funny story is how we ended up with the name “Jugl.” I am a transplanted New Yorker, and I love people who tell it like it is and don’t sugarcoat things. The original name for Jugl was KATBIA ˗ an acronym for “Keep All The Balls In the Air.” I started to have doubts about the name when no one could remember it (Kabia? The Cat thing?) Then, one of our early advisors who gloriously and bluntly said to me “Amy, you need a new name for the company. Yours reminds me of ‘labia,’ and I’m pretty sure that’s not what you’re going for.” Indeed, it was not! A few weeks of intensive brainstorming later, and Jugl was born (hat tip to my husband who came up with the winning idea). I am forever grateful to both of them.

What was your biggest challenge to date either personally or professionally and how did you overcome it?

The biggest challenge that I have faced was surviving the personal and professional maelstrom that was 2008. During that year I had a newborn baby and became the first person at my firm ever to take maternity leave (and I was Chief Operating Officer, Chief Compliance Officer and a partner of the firm). I flew back-and-forth from Chicago to New York almost every week to help support my mom as she was dying of cancer, planned and executed her funeral from 1000 miles away, and planned and executed a bittersweet baby-naming celebration one month later. Oh, and helped my firm navigate that pesky total financial meltdown — including the potential insolvency of most Wall Street counter-parties! I overcame (survived?) it by putting one foot in front of the other and (for once) NOT thinking about the big picture, but instead focusing at each point in time on the 3–5 next executable actions that would make progress on each front.

What does leadership mean to you and how do you best inspire others to lead?

To me, leadership is the ability to create a vision for a better version of the future and then get other people excited about joining you on the journey. When you lead well, you bring out the best in people and make space for them to use their insight, skills, and vision to improve on what you started thinking out on your own. My former business partners loved to say that “there’s no monopoly on good ideas.” Great leaders keep the vision in sight but hold it flexibly so that we can make it even better as a team. I endeavor to inspire others to lead by sharing the “why” behind what we are trying to accomplish and then creating a good balance of autonomy and support so that our people have space to lead and grow (not simply execute). I appreciate those who lead by example, which means big things like public speaking and making hard decisions, but also lower profile acts like singing the praises of your team whenever possible, rolling up your sleeves to pitch in when your team is trying to meet a tight deadline, and doing the little things that make office life civilized (like refilling the paper in the printer when you use it up).

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I was very close with my father, but he died while I was in college. For a long time, I was angry and sad to be deprived of such an important mentor and confidant, but now that he’s been gone for 25 years(!) I feel deep gratitude. His death taught me that life is precious and not to waste any of it if you can help it. More importantly, it turns out that the four main values he instilled in me as a teenager were most of what I needed to know to be successful: work hard, be a “mensch,” do what you said you were going to do when you said you were going to do it, and give back.

Was it difficult to fit your life into your business/career and how did you do that?

There is no “fitting life into your business/career” as I see it. Life is what we live every day, whether we are at work, on a glamorous vacation or home, sick. It’s harder than it used to be because the rigid line between life “at” work and “outside” of work has dissolved for most knowledge workers. The level of flexibility we have during the business day will vary based on our job and our level of seniority. But one of my core beliefs is that how we spend our time is a direct reflection of our priorities. Whether we are conscious or unconscious about those choices we make — that is up to each of us. Every moment of every day there is the one (or small handful of) things that we ARE doing and literally millions of things that we are NOT doing. It’s the ultimate FOMO if we let it be defined that way. I think happiness in the modern world is greatly enhanced by being fully (and hopefully joyously) immersed in the task at hand the majority of your time. I can’t say that I succeed with embracing JOMO (the Joy of Missing Out) all the time, but I aspire to!

Did you find that as your success grew it became more difficult to focus on the other areas of your life?

Wow, that’s hard to answer. Like many women, my success and my family grew at the same time. It’s hard, but one of my mantras is that people make time to do what is important to them. I try to make time for what’s important to me (and I notice and appreciate when others do the same). But to say that it is not more difficult would be untrue. It’s much harder to be a working parent than it was to work before I had any responsibilities with my children. If we don’t acknowledge that, we are doing all employees a disservice.

Can you share five pieces of advice to other leaders about how to achieve the best balance between work and personal life?

Here are five tactics that have worked well for me:

  1. Wake up early. Whatever you need to do to keep you sane and happy, try to do some of it at a set time each day. For me, that is waking up at 5 am most weekdays to exercise and reflect before the day is off to the races. There’s no other time that I have found to be pretty much entirely within my control. Thank goodness I am a morning person!
  2. Don’t worry too much about balance on any given day. Some days, weeks or months will tilt in different directions, but I view this as part of living a full, productive life. When I reflect on a week or month, and I feel the balance is off, then I adjust, but day-to-day “balance” for me is not a realistic goal.
  3. Plan ahead. My top time management tip for working parents is to plan out the family schedule in two-week increments (we do this every Sunday). I recommend mapping out the plan for all kids’ activities (what events, what they need to bring, who is driving), confirming evening plans and travel (including with your partner, if applicable) to determine whether you need extra babysitting hours, working on meal planning (we pick 2–3 recipes), etc. The key to this tip is doing it two weeks at a time. The week that is about to start is usually pretty firm: there may be a few additions or changes, but the events closer in time tend to be front of mind. Planning NOW for the week AFTER that is where the system shines. By focusing on what is coming at you the FOLLOWING week, you can avoid the massive pain of preventable last minute “fire drills.” It is WAY easier to find a babysitter or ask a friend for help or switch around a carpool or event, etc. if you have a full week’s notice. It only takes a tiny bit more time to get the two-week habit set up, but the time and stress it saves you by not having to drop everything when you realize at the last minute there is a conflict that you could have reasonably foreseen is immense.
  4. Keep your sense of humor. It won’t go perfectly every day, but that’s OK, and it’s an important message for our kids and our employees to internalize that, too.
  5. Don’t give up! How we spend our time is a direct reflection of our priorities. I think taking time to have a happy and full life outside of work (regardless of whether you have kids) is important, and I’m not ashamed of that at all. I have my best ideas about work when I’m relaxed and happy and often doing something else, like exercising. Don’t let work push you past your personal happiness balance over many weeks or months! And don’t quit. We need parents (especially moms!) to provide their leadership and perspective in the workforce.

What gives you the greatest sense of accomplishment and pride?

I feel the greatest sense of accomplishment and pride when I see the impact that having a strong working mom has on my daughters. My youngest was 8 years old when I started Jugl, and she printed a picture of herself giving me a “thumbs up” gesture and framed it with the words “Dear Mom, I just want you to know I think you are so brave to take on as big of a task of “starting your own [business].” You can see the image here. I cried when she gave it to me. I mean if ever that was a sentiment to capture what values I hope to be instilling in my daughters as a woman, mom, and entrepreneur — this was it all in one adorable Fujifilm Instax printout!

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Jugl is about making it easier to be a working parent (especially a working mom). That is the main influence behind the platform Jugl is building AND a major influence on the culture of the firm that we are trying to build. Honoring the “Jugl” between work & the rest of life is in our DNA. That is the movement I would foster! To honor the juggle!!! Not tolerate it or accommodate it but HONOR it, celebrate it and make it known to people that their ability to have a robust and fulfilling life outside of the office matters to their employer. In this movement, employers would respect people’s ability to find their own balance among & between all aspects of their lives (work, family, friends, health, spirituality, leisure, community service, etc.). They would firmly believe that respecting & honoring this in their team leads to greater loyalty and engagement. They would know that it keeps great employees in their workforce who might otherwise opt out. They would have total conviction that being a great parent (or caregiver or friend or volunteer) and being a great professional are not mutually exclusive.

What is the best way for people to connect with you on social media?

@Amy Rosenow on Twitter

About the author: Jacob Rupp is a coach, author, speaker, podcaster, and rabbi. He is the founder of Lift Your Legacy, a community that helps people live a more authentic life. He has a regular, syndicated column that appears in ThriveGlobal and Medium magazine. To learn more about him or to listen to the Lift Your Legacy podcast, search iTunes or visit his site:

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