Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur“ we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Michael Perry.
Michael Perry is the Founder and CEO of Maple, a family tech startup looking to ease the burden of parenting, freeing up families to spend more quality time together. Michael was the former Shopify product director and co-founder of Kit (which was acquired by Shopify in 2016). He left his role at Shopify in 2020, after becoming a father, to develop a platform that would change the world of parenting through technology that already exists for nearly every other industry.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Michael Perry: Truthfully, I don’t think there was an exact moment I got “started” in entrepreneurship. As far back as I can remember I knew I would have my own business. My uncle was a small business owner and guided me down the path of business and entrepreneurship at a very young age.
I eventually got into entrepreneurship in a real, tangible way after launching my own software company — which failed. That experience, although frustrating, spurred an addiction to create products that people actually use and found value in. I knew at that point that this feeling of innovation was something that I never wanted to have absent from my life.
Over time, this feeling only magnified and I had a desire to build better technology for small business owners. I evolved this idea until one of my companies, Kit, was acquired by Shopify.
It was ultimately in the process of becoming a Dad myself that I realized our greatest problem and our greatest opportunity in life is to care for one another and do better in raising the generations that come after us. Yet, it’s so insanely hard and with all of the technological advances we’ve made, the role of parenthood hasn’t been made any easier.
So for me, being an entrepreneur was just a deeply rooted part of who I’ve always been, it was never this “aha” moment. I did always think I would have a brick-and-mortar business until I fully realized my love of technology. From there, I found a way to tie technology to my passion for small business and further down the road found the intersection of technology and family which led me to building Maple.
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
Michael Perry: I believe there were two really clear “aha” moments. The first came when I realized that as a new Dad, the help I was looking for simply did not exist and that our tech revolution had totally skipped over parenting. This realization led me to the decision to quit my job and start working towards developing technology that would make all parent’s lives easier.
The second came when I really crystalized my thinking on the “how”. I felt so confident directionally that I took a photo of myself in the very moment. I realized the best way we could help make parenting easier was to understand the day-to-day tasks parents have and create better help for each of those responsibilities. I knew we needed to build a platform that worked with various, unique partners built into our app — making Maple the first parenting super app.
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
Michael Perry: Over the years I’ve met various entrepreneurs and asked myself this question many times. The answer I’ve come up with is that anyone can be an entrepreneur, the same way anyone can go to the park and play basketball or pick up a guitar and play for themselves. But to make it to the NBA or play at Madison Square Garden you have to have a natural talent matched with a tremendous amount of drive and discipline. So to me, being a natural-born entrepreneur means having the talent but the ambition and drive must also be there.
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
Michael Perry: When I was growing up,my uncle owned a video store and a jewelry store. He taught me so much about building a business and I aspired to one day own a brick-and-mortar business like him. My parents also taught me a lot about hard work and paving your own way in the world. When I wanted to start my first “mobile car washing” business at the age of ten or so, my parents very much encouraged the idea. Because of their support and encouragement, I’ve really never looked back in terms of running my own business.
What do you think makes your company stand out? Can you share a story?
Michael Perry: I think our mission to improve the quality of life for families is what makes us incredibly special and helps us “stand out” on its own. It has been incredibly humbling to see people so passionately join Maple and be so determined to move the needle forward for parents and families. At the end of the day, we are all family members to someone else — and the work we are doing is directly helping the people we care for most.
Maple is also special in that it prides itself in being a family-first company, which is apparent through our practices. Through proactively hiring stay-at-home parents and establishing “family flexibility hours” for part-time team members, we are proving our commitment to making space for parents in the tech industry and beyond.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Michael Perry: I believe there are different needed skills at different stages to be successful but these three things have been a critical foundation to my success (and ongoing development). Grit is incredibly important, especially when starting out. I have been told ‘no’ many times in my life and career and if I let that stop me I would not be where I am today and Maple might not exist. When you are passionate about something you need to find ways to move forward even when it is difficult or you fear others may not understand where you are coming from. It is your job to prove to them that what you’re doing is important.
Lead and creating with empathy has been key to growth and success for me. With Maple’s vision of making life easier for parents, it could not be more important to carefully and thoughtfully listen to the varying concerns and needs of parents. Everyone’s struggle is a bit different and being empathetic to these experiences is what will help us make Maple successful.
I have always made sure to stay curious. Technology is changing by the minute and with that society is changing. I think it is critical in being a successful business leader to stay curious and realize there is always more to learn and ways to adapt to new findings or perspectives. Those who aren’t seeking out knowledge and innovation, especially in their sector of business, will be left behind.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Michael Perry: This is a great question. I was once advised to hire someone but my gut told me that this person was not the right fit for my team. They ended up being a complete disaster and had a largely negative impact on our team culture and progress. Hiring team members have the ability to make or break you, and this person almost broke me.
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
Michael Perry: Burnout is far harder to recover from than people realize. Unfortunately, early in my career, I contributed to this by overworking myself and my team. I think it’s a very clear sign of poor sign of leadership to not be able to recognize when you are burning yourself, or your team, out.
My only tip would be to find a pace that is sustainable and a rhythm that people feel inspired by. If you can operate with a sense of urgency that doesn’t lead to burnout, then you’ve found the right place. Only disrupt that pace for an opportunity that can’t be ignored — and that the entire team can get behind. Lead collectively on this change and build everyone up to the required pace together.
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Michael Perry: “Proof is in the pudding.” It may be an unpopular opinion but credibility and authority are earned, not given. This is true for trust as well. On how to build trust internally within your team, I recommend reading about Tobi Lütke’s “Trust Battery” concept.
Can you help articulate why doing that is essential today?
Michael Perry: The more trust, credibility, authority you build the faster you can move as a team and as a company. I also believe that to build on these three pillars, it is necessary to articulate a clear vision and provide your team with the right tools and resources to follow through on that vision.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Michael Perry: The inability to balance patience with urgency — giving up way too soon.
People massively underestimate how much time it takes to “make it” or “breakthrough”, so they give up way too soon. As time goes on and people become successful, their inability to take a step back and change their position can be a fatal flaw. Hubris is the death of many.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
Michael Perry: Entrepreneurship is probably one of the only jobs where you can think you’re a genius, an idiot, going to become rich, going to become poor, going to change the world, and think “this is the dumbest idea ever” all in the same day. Sometimes hours apart. It is an incredibly taxing job knowing your decisions can make or break a business and that you are financially responsible for your employees and your shareholders.
As much as you’d like, there is no “turning off” from this reality or set of responsibilities.
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
Michael Perry: My favorite day-to-day highs are the rush of product launch days when the team gets to see how the world responds to their work. But nothing beats the high of someone telling you they love your product and how it has changed their life.
An all-time high for me: Selling my company, Kit, to Shopify in 2016.
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
Michael Perry: I’ve launched features and products that no one has used or thought were totally stupid, and that feels pretty terrible. You start to doubt whether you “have a business” or any shot at building one.
I have had 50 different investors in a row tell me “no” and that can significantly compound that feeling in the worst of ways.
Based on your experience can you tell us what you did to bounce back?
Michael Perry: Quite simply, every time I felt like I was at “rock bottom” it felt harder to quit than to get up. I just refocus and try to push myself a little bit harder.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
- Build the strength to listen to your internal voice: quiet the “demons of doubt” as best as possible.
- Never measure success day-over-day or week-over-week: look back on months/quarters/years.
- Do not rely on the hope strategy: pay attention to the good and bad of your business and take action
- Remember why you started.
- Always invest in your mental health. I strongly recommend meditation or an investment in an executive coach.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
Michael Perry: I would define resilience as one’s ability to pursue tomorrow’s dream without giving up on today’s challenges.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
Michael Perry: My family has overcome every adverse situation thrown at them. Growing up, my parents were faced with endless challenges of being young parents with no sense of financial comfort. My parents had (and still have) an unexplainable work ethic and have always taught me that regardless of your circumstance, you have to fight for what you believe in and want.
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
Michael Perry: I think so. For better or worse, I believe there’s no problem that I cannot work to fix.
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Michael Perry: Building a business is far harder than anyone can anticipate. Without a positive and optimistic attitude success is rare (if ever) reached.
Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?
Michael Perry: “Be a first-class you, not a second class someone else.”- My Grandma
How can our readers further follow you online?
Michael Perry: I am @michaelperry on Twitter and Instagram!
This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!
Did you enjoy this interview? Check out similar interviews:
