Michael Arrieta has had exponential success in his relatively short career. As a Cutco sales rep, he was the #1 new sales rep in the company during his first year. He became one of the top college-student sales reps in the history of the company before graduating from the University of Alabama. Michael’s first corporate experience was with Wyse, a company which was purchased by Dell, where he was able to leverage his experience, effort, and results to advance to Chief of Staff in a short period of time. He got onto the radar of legendary Silicon Valley entrepreneur Keith Krach, and eventually moved to a role as Keith’s Chief of Staff in the early days of DocuSign. Michael was truly one of the key players in DocuSign’s meteoric rise to market dominance, and he advanced as far as Global VP before departing from the company recently. He was even named to Forbes “30 Under 30” in 2016. Now, he has started his own holding company, Garden City, for the purpose of buying and transforming service businesses all across the Southeastern U.S., bringing them new culture, improved technology, and increasing opportunities and benefits for their working-class employees. Michael is also the co-Founder of New Story, a non-profit whose mission is to end global homelessness. This guy is an absolute superstar in business and in life.


Q: Tell us about your time in Vector, particularly the lessons you feel have continued to help you in your great career

  • A friend of mine was with Cutco, I was in college and was already looking to make money.
  • My family was having some difficulties, financially and medically. I was looking for a career that would help my family. My friend said with Cutco, “you could really control your own destiny and be successful as you wanted to be.”
  • That’s how I got involved. I started working with my friends and family. I’ve always realized the power of a referral more than anything.
  • That’s what led me into it and getting involved with Cutco. Getting into a good start. Having a great manager, Cathy (Christen), when I was so young. She taught me a lot of great things around sales, building rapport, and all that. So, it was a great year to start.


Q: Why do you think you were so successful a young sales rep?

  • First, the situation I was in. Some things came with perfect timing, but I really felt my family was counting on me to deliver.
  • Also, I came from a low-income family (less than $50,000 per year). So, I was naturally curious about everything. I would ask questions to create rapport.
  • By the time we were 15-20 minutes into an appointment, their guard (potential clients) would quickly come down because we had built rapport.
  • Thirdly, once out of the gates, I would always set the tone of what success looks like to me. What success looked like to me wasn’t you buying a whole set of knives. Success looked like I need people to see. Because knowing if I could see the right number of people, I would eventually sell the right number of knives. I was like, “if you don’t want the knives, you could refer me to some other people who did,” and they would immediately come down and say “talk to me, what do you have.”

Q:  After college, you got into a company that was acquired by Dell, and you had a nice run there at Dell. Tell us about that.

  • There was a critical inflection point after college, where financially I was doing great, making 6-figures every single year in college. When I was graduating, the biggest decisionI faced was, “should I continue to work with Cutco, which was a great option, or do I want to go down another path, where I had to take 2-3 steps backwards, and hope I would take 10 steps forward.”
  • I would say to anybody, only you know that answer. It’s a difficult one to make, and seek wise counsel. People you really admire, their life, their character, and their values. It’s what I did and It was a difficult decision because when I was a senior in college, I was making 6-figures and all the jobs coming off school were offering me ½ of that.
  • Getting good wise counsel, I was able to make that decision.
  • When I moved to Silicon Valley, I joined a startup called Wyse. What I really didn’t want to do was to go to a company where I was just another serial number. I feel the experience you get with Cutco, especially to the level I was fortunate to play at, is a real experience. When you make this kind of transition, make sure you join a company that’s valuable.
  • After a year and a half, we were blessed to sell to Dell, and I was lucky to get an opportunity to become the chief of staff. I was responsible for a couple of things, including the integration of our acquisitions. I honestly didn’t know much about it, I was very, very young, but Dell proffered me the platform to learn that.

Q: How did that lead you to DocuSign? You had an amazing time at DocuSign. Tell us of your experiences there and what you learned through those years.

  • One of our venture capitalists was also an investor at DocuSign, and he referred me to be the chief of staff for Keith Krach. I think I love the definition of luck as “when preparation meets opportunity.” I think that’s a big factor in getting high profile career opportunities at a young age.
  • I worked real hard. I was the first one in and the last one out. I made sure I was a quick learner.
  • I think Cutco gave me the foundational framework. If you could dream, you could probably become it. A bit of luck, a bit of opportunity, and a lot of preparation.

Q: What was it like taking DocuSign from $0 value to what it is now ($5 billion)?

  • When I joined DocuSign in 2014, there was a big opportunity. Everyone was trying to “digitize” everything they were doing.
  • We were in the perfect place, at the right time and with the right product. We had an ideal problem market fit.
  • We also had an excellent go-to-market strategy. In order for us to become a “verb,” we had to really get all the largest Fortune 100 companies as customers. We wanted to be the global standard. Our investment strategy was very strategic. Keith always said, “keep your friends close, and your enemies even closer.”

Q: Now you’re an investor and advisor to multiple companies including Impossible Foods (worth $3 billion), Blue Bottle Coffee, etc. and you’re starting your own holding company called Garden City. Talk about what your days look like now.

  • The investments started when I was in Silicon Valley, and there were so many great leaders, starting so many great things. I just saw the same type of opportunity that DocuSign had.
  • There was a real problem market fit. They were just solving a real-life problems.
  • Number 2, they had the right leaders, someone that could actually execute the vision.
  • Number 3, they had the right strategy to make that happen.
  • So, I started investing in Impossible Burgers, then called Impossible Foods, Blue Bottle Coffee, etc. and it sparked something in me. I was really excited about working with these companies, helping them grow.
  • I started realizing my passion in life really was seeing small things flourish. I’ve always had a deep passion and excitement from boring, “unsexy” service businesses. Car washes, drycleaners, landscape companies, you name it.
  • That was the vision of Garden City. To create a holding company which exists to enrich the lives of the working class. We do that by acquiring family-owned service businesses. We then put a culture that’s all about purpose, belonging, excellence and we technology-enable the companies through all their operations, processes, and systems. This is all about creating the next “Cutco-like” companies of the world.

Q: What other advice would you have for people who want to experience the same success that you have achieved?

  • One big thing is just authenticity. I believe God made each of us in a very unique way. Be yourself. Don’t try to be something you’re not. People love authenticity. As soon as they see that you’re not trying to put up a front, that speaks more value than anything else. Become the best version of yourself
  • Number 2, always seek wise counsel. That’s probably something I have too much.
  • Number 3, hard work. anything that is worth doing takes hard work.
  • Lastly, set a vision of excellence. Figure out your level of vision and hold on tight to that.

Q: Tell us about your involvement in New Story

  • When I was at Cutco, I was honestly not generous and I wish I had been. 5-6 years ago, my best friend and I were like, Hey, there are many non-profits we don’t agree with how they go about doing business. What don’t we like about non-profits?
  • 1, we don’t like giving money to them and it goes into a big black hole. We don’t know if it impacts. We don’t know the level of impact or contribution they make.
  • We realized what it could look like if we created a non-profit; New Story.
  • We said we wanted to eradicate homelessness from the planet. It would be real cool if you give $100 and out of that, 100% went directly to the cause. We then went, to give that $100, you would get to see what family it was donated to.
  • Once the family is in their new home, we actually take baseline data to tell you, before the family was homeless, their children were sleeping x hours of night, their education level, their financial level, their healthcare level etc.
  • That’s what we created 5 years ago and said, we want it to be the most innovative non-profit in the world.

Q: As you look into the future, how do you aspire to change lives through your work or through your influence?

  • It’s all about making a positive impact. Through New Story, we have built about 3,000 homes in Haiti, El Salvador, and Bolivia.
  • About 2 years ago, we said let’s think even bigger, let’s actually instead of building our own homes, why don’t we enable other non-profits in the housing sector to build homes cheaper.
  • We said, let’s create a 3D home printer that literally pours out wet cement and prints the entire structure of the house including all walls, window frames, and doorframes by itself with no labor. We are now creating the world’s first 3D printed community in Mexico!


  • Mike talked much about authenticity. The benefit of becoming your best self. Not a version of someone else, not trying to be someone you’re not. Not trying to misrepresent who you are. Being the best version of yourself.
  • Also, be in a position of envisioning if you can take a couple of steps back to take 10 steps forward. There is going to come a time when you decide is this the place I wish to stay or do I wish to go somewhere else. Figuring out what you want, what’s the best path.
  • Think about who you’re around who could be the most profound influence in your life, and how you can get more exposure to them.
  • Lastly, hard work is as well a big secret of what it takes to get to where you want to be.



  • Youtube: @NewStory
  • Home – Apple+

You can learn more about Michael’s new company, Garden City, by visiting here.

You can support New Story here.

Show Notes for this episode were provided by Brian Njenga.

To learn more and get access to all episodes, visit our podcast page!


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