A Founder's Journey Includes Building and Caring for a Team with Art Shaikh

A Founder's Journey Includes Building and Caring for a Team with Art Shaikh

MP recently chatted with Art Shaikh, founder of CircleIt. Shaikh spent 20 years building relationships and high-performing teams, including in his last role at Salesforce. He has always had an entrepreneurial drive, and his dream came true in 2018 when he was able to start CircleIt. CircleIt is his passion, and he has built a diverse team of experts to help him bring it to the masses.

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

I have learned a lot during my time on this journey. I realized that I could do almost anything, but I have found it best to ask for help and bring in people to help along the way. I needed to learn the basics of specific tasks and then find the right people to execute them at a high level. 

I have learned about loyalty, given, and received. I have always considered myself loyal, and seeing how many friends and family were early supporters of my mission was overwhelming. As the team grew, they were extremely loyal, some moving across the country to grow the company. I think of these people as family and treat them as family.

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur? If yes, what was that experience, and how did you overcome it? 

This journey can sometimes be lonely, but not because you’re physically alone. I think the sense of loneliness gets confused sometimes with the fact that you need to be your best advocate in every sense. You have to be the one pitching to investors. You have to be the one that manages the team, and you have to be the one that puts in the hours. Early on, you have to be the one that believes in yourself and your mission. Eventually, others will come around. Now, with how we have grown, I never truly feel lonely.

The Psychological Warfare 

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur?

I’ve had many sleepless nights and long days where I have worked 18-20 hours. Because this mission is so personal to me, it isn’t really a “job” or anything along those lines. I don’t have the “exit strategy” many founders have, where they build up a company to make a bunch of money by leaving it. 

CircleIt was born out of a gift my father left, where he was able to be present for my mom, my siblings, and his grandchildren even after he passed away. Because of this, the mission is a part of my DNA, and I think that is why I haven’t come across the common entrepreneurial issues of low self-esteem or low self-worth that so many have faced. Although, there is always some insecurity I have met throughout the process. I carry my mission in my heart and soul. The validation from friends and family that this will genuinely solve a global problem that affects everyone helps alleviate some of those insecurities.

What are your three biggest fears as an entrepreneur, and how do you manage those fears? 

I think survival as a company is always a fear of any entrepreneur and probably my biggest one. I have been fortunate that when those fears become intense, I am reminded in some way that a mission is being served that is bigger than myself. I feel that because I’m working to make the lives of others better, the universe will always carve out a path to success.

While it may not be a “fear” in the traditional sense, I feel like I want to be doing more for my team. When I hire people, one of the major things I look for is a resonance with our mission. Because these people are family to me, I want to be sure that we are always doing the right thing for them. Being an early-stage startup, there are constraints as to what can be done, so part of the mission is to ensure that the team is well taken care of and given whatever they need to be successful inside and outside of work. I find the solution for this is that I keep working with a focus on doing right by them.

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In a way, the fear of not scaling fast enough is related to the other fears I mentioned. Because we are a software company, speed is always a necessity. And when I talk about scaling, I mean it in every sense. From quickly growing the business, to bringing millions of members onto our platform in a short period, to hiring additional team members to make the work happen faster, to being hyper-aware of team member burn-out – these are things that I worry about. When I am able, I try to give the team some time to enjoy a day off or send them home early. We have a hybrid work model, which I wanted even before the COVID pandemic because the rate of burnout in the tech industry is high. It is always impressive that I have to beg certain team members to close their computers for the day. When I see that sense of loyalty to our mission, it helps me forget the fear. 

The Mistakes

What are three mistakes you made early on as an entrepreneur, what did you learn from them, and how can others avoid these mistakes? 

1. I Allowed Someone To Tell Me Something Couldn’t Be Done

Mistakes are inevitable. I allowed someone to tell me something couldn’t be done. I won’t go into specifics, but a founder can’t accept that answer. So I needed to investigate more, find the solution, and find the right people to execute.

2. I Thought I Could Do Everything Myself

Another mistake was thinking I could do everything myself. A lot of being a founder is trial and error. While I needed to understand the basics of everything, having to do it daily would get me bogged down. So to lead, I needed to build a team and trust them to execute. I am lucky because I have experts in many fields that accomplish things reasonably unheard of.

3. I Was Not Involved in Certain Aspects of Our Operations

Along those lines, the opposite mistake was also made. Not being involved in certain aspects of our operations was also a mistake. While I don’t believe in micromanagement, I know I need to be informed about what is going on at every level. I suspect every founder falls into this trap at times. We occasionally have so many considerations to consider that we allow some aspects to be overlooked. 

What are three things you see that are often overlooked by entrepreneurs you encounter, and how can other entrepreneurs be aware of these things from the beginning?

1. Many Entrepreneurs Think the Only Way To Get Funded Is To Seek Venture Capital

One major thing is regarding funding. So many entrepreneurs think the only way to get funded is to seek venture capital. However, these VCs are the only middlemen that secure financing for you in exchange for a large chunk of your company. My advice in regards to funding is to work. My career at Salesforce enabled me to raise the seed money I needed to start my business. While the trend is always to talk about founders in their 20s, what ends up happening is they lose their companies to VCs by giving 20-40% upfront to secure funding. By not starting CircleIt until I was in my 40s, I had more perspective and economic freedom to secure my financing the way I wanted to.

2. Friends and Family Rounds Are Often Overlooked

Also, regarding funding, I think friends and family rounds are often overlooked. Your true friends will always do two things: be honest with you, and support you. The response was overwhelmingly positive when I proposed my idea to friends and family. And I knew I could trust their instincts and feedback. This not only helped me start to grow the company but also gave me the validation that this was a service and product that the world needed.

3. Contracting Specific Jobs Can Cost You in the Long Run

While initially, using contractors for most jobs is essential, continuing this long-term can cost you more than you save. For example, while it would be far less expensive to contract out my marketing services to an agency, the turnaround time and lack of transparency become more costly than what it saves in terms of salary.

CircleIt team photo
CircleIt team photo with founder Art Shaikh (fifth from left) / Photo courtesy of Art Shaikh

The Successes

What are three seemingly insurmountable obstacles you’ve faced as an entrepreneur, and how have you overcome them? 

1. One of the Hardest Things To Do in the Tech World Is To Get Press

With so much noise and competition from within your industry and the world, it seems like a steep hill to climb. However, what I’ve discovered is that once you make something a priority and focus your efforts on it, change happens. We started to see coverage after we assigned the right people to the job and gave them the freedom and tools to succeed.

2. Almost All Tech Startups Face the Same Challenge Regarding the Failure Rate

This is well-known to the investing world. So you have to overcome this ingrained narrative that almost all ideas fail and that you will too. I have always told my team that if we keep putting our heads down to do the work, the proof will override any doubts. And so far, that has been the case. 

3. It Seemed Impossible To Get Traction While Working a Full-Time Job

At first, I was working my full-time job and trying to get the company started. It seemed almost impossible that I would give up my career to go all-in on this journey. I think this is common for any founder, especially those in their 40s. There is a bias toward youth in the tech world, and there are many reasons for that. This is why middle-aged folks don’t find most tech startups. But I knew it would be an advantage because I had experience on my side and an idea that would change the world on a fundamental level.

What are three ways you have managed to boost your productivity without causing burnout?

1. I Cut Out All the Noise in My Life

I had to move forward at the speed I needed to. What ends up burning people out is not prioritizing their lives. We want to give attention to everything, both personal and professional, and when founding a company, it isn’t possible. Once you realize you can’t do everything, it is easier to set aside certain things.

2. From a Company Standpoint, I Have Added Team Members To Help Keep Specific Individuals From Burning Out

In a startup, everyone is asked to do a lot, and in many cases, unfortunately, too much. However, because I keep myself ingrained in the day-to-day of the company, I can tell what is going on with my team and adjust accordingly.

3. I Try To Give Everyone Whatever Time I Can Back to Them

Whether cutting out earlier on a Thursday or taking the team out to lunch, I want our people to feel fulfilled in their work and fulfilled as people. So, where I can, I attempt to give back to the team because they give so much of themselves to work.

The Advice

How can newer entrepreneurs develop a healthy work-life balance even when it seems like an impossible task?

Whether it is healthy or not depends on the individual. However, one of the things I do know is that without your health, you are not going to operate optimally, which is a detriment to your business. I try to remember to take time with friends and family, which might sound cliche, but it is also something that does help. I am fortunate that everyone in my life knows what I am doing and why I am doing it. Once that is clear to everyone, it makes things much more manageable.

What three key pieces of advice would have made your entrepreneurial journey easier, and why? 

“You can’t do it all.” If I had truly understood everything that went into what I was doing when I founded the company, I would have known this to be true. But I wasn’t aware of everything and quickly learned that I needed to seek the right help to bring the dream to fruition.

“Trust your instincts, but always verify.” Early on, I would second guess things often. I would hear a piece of advice that conflicted with what I thought to be accurate so that I would make changes. More often than not, this would end up causing a slowdown. I learned to start trusting myself more, which has worked out quite well.

“You never regret being kind.” While I don’t ever think this was a problem, I think it is something that bears repeating in general. I have yet to regret being kind in my professional life. I want my team to have fulfilled happy lives and always be known as someone who treats everyone the right way.

Cover photo courtesy of Art Shaikh.

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