Saturday, November 5, 2022

Thoughts on Taking the Leap To Be an Entrepreneur

As with a lot of my blog posts, it’s half diary for me, half wanting to share with anyone who is interested, the why behind career moves, insights into some of my experiences and just generally things I’m learning. As of August of this year, for the first time since college I have taken the entrepreneurial leap and started my own company, Beeloo. If you're interested in what it is and where the inspiration for it came, you can check it out here.

In this blog post, I’d like to share more about how I came to decide to take this leap, which some consider to be drastic since I’ve worked my whole career for tech companies with at the smallest 500 employees, but usually large public companies with several thousand employees.

To fully understand current decisions, we got to go back to my first job ever. In high school, I had a moderately successful lawn mowing business in my town in the suburbs of Austin, Texas. I had a trailer, employees, commercial equipment and even a few commercial contracts. I earned more cash than a teenager should have, a lot of fun and learned many valuable lessons (like don’t take calls from a customer during a nap because you won’t remember what they said or who said it when you wake up). After that positive experience, it was only natural I wanted to continue being an entrepreneur for my career.

Once I got to college I focused my extracurricular activities on the goal of being an entrepreneur. I was the President of the undergraduate Entrepreneur’s club for my junior and senior year. As I got closer to graduation, the economy started to have a complete meltdown. (I graduated in 2009). I think I have a decent tolerance for risk but watching the housing crisis and everything else meltdown around me had me reassessing my plan. I accurately assessed that I had no money, no real skills and barely a professional network. It started to feel too risky to bet everything right after graduation. Ultimately, I decided I’d have to take the leap at a later stage in my career and I got my first entry level marketing job a few months after graduation at Salesforce, moved to San Francisco and started flying down the technology marketing career path. I remember a few friends and mentors being shocked because I had seemed so determined to start my own company. In fact, I remember talking through whether I should take the entrepreneurial leap with one of my professors and he told me “if you don’t become an entrepreneur now, you never will.”

The entrepreneurial itch was always there as my career progressed. I got more experience, built my network and was saving my money. I got an MBA and a few years later I made a riskier career move by joining a late stage high growth company that most people at the time had never heard of, Zoom. After four extremely intense years at Zoom, I felt my time at Zoom was coming to an end and it was time to scratch an itch, but the entrepreneurial itch was not the only career “itch” I had. I’m also interested in the public sector and public service. I had a goal for a long time to apply for a 1 year MPA program, which I explained in more detail in a blog post. After leaving Zoom in 2021 I went back to school full time. I loved my experience during my MPA program but of all the career paths and jobs I explored only one public sector job really stood out to me, which I pursued unsuccessfully. The timing did not feel right to go all in the public sector and public service, though my interest only increased during grad school.

During my year in grad school, I talked to a lot of friends and mentors to get their take on whether I should take the entrepreneurial leap after graduation. I constantly got two very different pieces of advice. One was “go follow your dreams, you're a go getter, I believe in you, if you want to start a company, go do it.” The other advice was “this is a bad idea, you're throwing your career away, go join another late stage company like Zoom, but at a more senior level pre-IPO and make a bunch of money. As an entrepreneur you could throw away the prime years of your career”. I fully acknowledge that if I was optimizing for corporate career growth or money, joining another high growth late stage company for someone like me is a no brainer. Part of me really wished that was something that I was excited about, but I just could not get excited about going down that path again.

My family situation and where we wanted to live also factored heavily into the decision. We have moved 4 times in the last 4 years across 3 states and with my oldest being 7 years old, we were feeling the need to settle down geographically. Before moving to Boston for grad school, we had bought a home in a suburb of Raleigh North Carolina, and really felt like that was a place that we could call home. Part of the appeal of North Carolina too was that our family “burn rate” could be so much lower than if we would have stayed in the Bay Area or settled in another large city. The tech scene in the Research Triangle is vibrant and growing quickly, making me want to be an active contributor to the community. Lastly, you work like a dog as an entrepreneur, but you get to decide where your company is based and you have ultimate flexibility, which is very appealing for my family given the age of our kids.

Years ago, after my MBA I worked at LinkedIn and I remember grabbing lunch with a colleague. Her and her husband sold their company to LinkedIn. I shared with her my entrepreneurial ambitions and she very bluntly said, “if you want to be an entrepreneur, just go do it, you don’t need any more notches in your belt.” That advice really stuck with me.

Overall, whether it be money, career or life decisions I try to think really hard about how much I will regret not taking a certain path and how irreversible the decision is. This all led me to taking the leap at this stage of my career. It might seem riskier, but it feels A LOT less risky than when I graduated from college. I have marketable skills and a deep professional network. This will help me with my current start up but also if I decide to return to a corporate job. I think one thing people worry about the most about taking the leap at this stage of life is money. You have to think about your bills, mortgage, paying for college for kids and healthcare. Since this is something that has been in my career plans for a long time, we’ve prepared financially, we can’t do this forever but given our low family burn rate we can give it a good shot.

Sometimes I envy people who have careers with a singular path, purpose and goal, but I have come to terms I’m not one of those people. I have a lot of things that interest me and if that means my career zigs and zags, that’s ok with me. Most startups fail, but I’m confident that regardless of the outcome of Beeloo this was the right path and decision for me at this time. If there are any aspiring entrepreneurs out there reading this, I hope this gives you the courage to take the leap and be comfortable with some intelligent risks.

Monday, May 9, 2022

What It Was Like To Do a Mid-Career Year MPA Program at Harvard’s Kennedy School

If you're wondering why I did this program to begin with, I explained it in another blog post that you can find here. I’m writing this post as a bit of a journal for me and to help anyone interested in a deeper view of what a program like this is really like. Going into the program I had three main goals that I had written down during orientation that I used to focus my time and energy. Here is what they were.

1. Make sure this is a positive experience for my family
2. Build relationships
3. Focus my time/energy in exploring new areas

For the first goal, this one happened way more organically than I ever thought. My wife and I have three kids under 7 and this would be our third move in three years, so we were pretty worried about what this experience would be like for the whole family. Luckily, I had got connected with some Harvard Business School students that also had kids and they gave us the best advice, which was to live at Soldier Field Park (SFP). SFP is Harvard campus family housing that is basically part of the business school, but only a 9 minute walk across the Charles river to my campus too. This ended up being an incredible decision. Graduate housing is done through lottery, but we were lucky enough to get a 3 bed, 2 bath apartment. It’s pricey, but it was worth it. We had instant community because our building was full of 2 and 3 bedroom apartments so there were kids everywhere. Not only that, but there was a playground basically right outside our door. When half of your neighbors also moved in at once too, it’s easy to make friends. It also meant we had access to all the amenities on campus and could walk into Harvard square to hang out or to eat. There was almost always something fun going on close by. After a pandemic year of being recluses, we made up for lost time with a vengeance. I’ll share more about Boston/Cambridge later in the post, but my Bay Area born wife, who is a tough judge of cities, absolutely fell in love with Boston. 

Our oldest was going into first grade and ultimately decided to put him in a private catholic school in Cambridge. We had never considered private school, but we home schooled him for kindergarten because of COVID and the lottery system for the Boston public schools created a lot of uncertainty, so we decided to do it. It turns out, most of the school aged kids that lived on campus went to private schools. He had a positive experience and we were even able to carpool with other kids in the neighborhood. Overall, we were really quickly able to make friends and build community through our church, classmates and neighbors. The business school in particular has an incredibly well organized and fun parents club called Crimson Parents that we participated in.

I had gotten the advice to really prioritize relationships with my classmates to maximize my experience. As soon as I met my classmates, I was in awe. It was such an incredibly talented, kind and diverse group of individuals. My program was geared towards “Mid-careers” so the average age of my classmates was probably ~40. About half of the 200 students in my program came from outside the US. In my class we had a Nobel Prize winner, a winner of multiple Emmy's, a professional dancer, musicians, doctors, diplomats, soldiers, lawyers, and the list could go on and on. The most inspiring thing to me though was that everyone was committed and wanted to be an active participant in the world around them, for good. No one talked about salaries, few talked about reaching career milestones, it was all about the issues or causes they cared about. Coming from a pretty capitalistic Silicon Valley career so far, it was a breath of fresh air and very inspiring to be so surrounded by those kinds of people. Being around those kinds of people made me want to do more for the public good, which is exactly what I had hoped for. I must admit that at times it was easy to get down as we studied some of the world’s most challenging problems. There were issues that I became much more acutely aware of, like climate change or I’d found out about a group of people that have been systematically oppressed that I had never even heard of like the Rohingya people. That part was so different from my MBA. An MBA is all about the potential of businesses and growth, but in the end, this is the world we live in and seeing such passionate people tackle some of these problems gave me hope that we’ll figure much of it out.

I’m a pretty social guy, but trying to balance the incredible social opportunities and home life is always challenging. I tackled this by setting some boundaries (things like, almost no evening classes) and being proactive about organizing social events that worked on my terms. I did a lot of “coffee” chats and lunches during the week and had to pass on a lot of week night 6pm dinners/happy hours. I also organized two class trips with classmates that were a mix of fun and meeting with alumni and organizations of interest. One trip was to DC in the Fall and another to NYC in the Spring. All and all, I feel like I was able to make many lifelong friends. One of the things I appreciated the most was how quickly our class became cheerleaders for each other. In our class Whatsapp group, almost every day someone is highlighting a classmate's work, or achievement and the whole group is full of positive encouragement for one another. 

A big part of coming back to grad school was to explore the public sector, public service and a variety of other interests. In a one year program you really don’t get to take that many classes, so it was a struggle to decide which ones to take each semester. There were only three required classes in three different buckets, but each bucket had like 20 classes in it, so in reality you could take just about any classes you wanted and still meet the graduation requirements for my program. There were almost twice as many classes as I was interested in, than actually fit in my schedule. There were a lot of interesting classes particularly around leadership that I did not take because they were similar to classes I took during my MBA. I wanted to focus on new topics that I was not exposed to during business school. Below you can find the classes I took, which ones were my favorites (highlighted in yellow) and a little bit about each one. Some of these were half semester classes, which is why I have so many classes in only two semesters.

API 205Politics and Policies: What Can Data Tell Us?Hughes HallettI had to choose one required quant course and this is what I choose. It was a great refresher on stats and analysis all in the context of really interesting policy or political case studies.
IGA 505Solving Tech's Public DilemmasCarterSecretary Carter is a former US Secretary of Defense, it was nothing short of incredible to sit in his class each week and look at the tech industry through his eyes and experience.
IGA 355MMigration and Human RightsBhabhaI've also been interested in the refugee crisis for a long time, it has been my issue and charitable cause of choice, but I did not know much about it. I really enjoyed just being in a class I did not know a lot about and soaking everything in. Learned a ton and more committed than before to doing what I can to help refugees of all kinds around the world.
DPI 640Technology and the Public Interest: From Democracy to Technocracy and BackSweeneyThis class studies technology and society clashes, it was very interesting to look at technology development in terms of its impact on society, especially after spending most of my career in Silicon Valley.

MLD 342Persuasion: The Science and Art of Effective InfluenceOrrenIn between fall and spring you can take a two week accelerated class where you meet every day for two weeks. I took this class and enjoyed it a lot, it was a great refresher on the soft skills of leadership.

IGA 236Cybersecurity: Technology, Policy, and LawSchneierOne of my favorite classes, Bruce Schneier is world renowned and just a knowledgeable and funny professor. I had always wanted to dive deeper into cyber and this was a great class to do it.
MLD 831Entrepreneurship and InnovationCavanaghIn this class we work-shopped social innovation business ideas, it was a small class. Really enjoyed seeing all the different types of businesses you can create for the social good. There are so many ways to use entrepreneurship to do good and we got to study a lot of different models in this class. I built out a business plan for a specific idea that I had during this class.
DPI 896MCrisis CommunicationsHaberReally enjoyed this class, got a bit of PTSD as I relived my time at Zoom during the pandemic, but really good still to have if you're ever going to be in a leadership position.
DPI 831MOp-Ed WritingGreenThis was a half semester small class writing workshop where we learned how to write op-eds, the structure, pitching and refined several op-eds we all wrote in the process. Only writing class I had every taken like that and LOVED IT!
HBSMBA7475CS50 for MBAs
In any graduate school at Harvard you can cross register. This was the only class I did not take at the Kennedy School. This was a entry level computer science class geared towards managers. I had always wanted to take a computer science class. Really enjoyed it and learned a lot.

Between my classes, classmates, attending random lectures and events across campus I got to dive into so many topics I have been interested in, but had not had the time to go deeper. A few favorite moments, hearing from US Cyber Command, a discussion about the Israeli-Palistenian conflict, hearing from elected officials and listening to lectures on current event topics like the war in Ukraine.

A few words about the Harvard community in general. The first day we moved in, I met a next door neighbor. We got talking and I asked him all the standard questions, what were you doing before and what are you hoping to do after school. In that short intro conversation, I found that he was a former Navy Seal hoping to one day build a hotel in space. In a lot of ways, that sums up what it is like to be in this environment. Surrounded by incredibly accomplished people with some big goals.

In terms of academics, there is some truth to what they say about places like Harvard that “the hardest part is getting in”. I was a pretty average student in high school, better in college and even better during my MBA, but I was never the stereotypical straight A student that aced standardized tests. For me, believing that I could attend a school like Harvard only started to creep into my mind once I moved to the Bay Area after my undergrad and worked with a lot of folks from Ivy league institutions. Working with them took away a lot of the mystique around what it takes to succeed at those schools. I thought my colleagues were smart, but I realized I could keep up. As I did well professionally I think I just generally had more confidence in my capabilities, even if I totally sucked at taking standardized tests. In fact, my GMAT score was so low that BYU grilled me about it during my MBA admission interview. I found that my time at BYU prepared me well academically to do well in my classes at Harvard. There were classes where it took a lot of effort and work and some classes where it did not take that much effort. I also selected the classes I was most excited about and interested in, which were rarely subjects that I would not have excelled in. I think as an older student you are able to focus better and not stress out as much, so the academic side of it was not a stressful experience for me. I’m sure I would have completely drowned in an advanced econ class at Harvard. I felt like my best Professors at BYU were just as good as my best Professors at Harvard teaching wise, but I think the biggest differences comes from the professional renown and experience of the Professor. At Harvard it’s just often at a different level, same with my classmates.

Harvard was pretty serious about their COVID restrictions. Luckily we had an in person class for just about the entire year. We did not ditch the masks until the end of Spring semester. There was a pretty formal testing program where you usually had to do a COVID test twice a week. There were some limits to different kinds of gatherings and canceled programs, but overall I’m guessing I got 85-90% of the pre-COVID experience. I’m glad that I decided to go this year.

There are some funny quirks about Harvard. One of them is that once you're in, it’s really easy to complain about Harvard. I think people have such high expectations going into it that a lot of folks are shocked to find out that not everything is perfect, but no organization is good at everything so sometimes we all had to remind ourselves of that.

Politically, I’m pretty moderate. I did my undergrad and MBA at BYU, which is generally pretty conservative leaning so I was bracing myself for whiplash going to a place like Harvard which I expected to be pretty liberal. It is in general, but not as much as I would have thought. I was pleasantly surprised, especially in the Kennedy School to hear some diversity in thought. Don’t get me wrong, there is a strong liberal under current and there were some discussion topics that seemed to be avoided because any disagreement with the general current would unfortunately not result in a productive dialogue, but the majority of my classmates I personally found to be very open minded, diplomatic and thoughtful. As a 2nd generation Cuban immigrant, who’s Dad fled communism, I tend to be in the “Pro-US, with all of its imperfections camp” and there was much more of that than I thought there would be, especially on the national security side of things. Many of my classmates were from different branches of the military which I think helped to create that feeling. Also, as a person of faith and this being my first experience in higher education that was not faith based, I was pleasantly surprised how all faiths were embraced. I felt like I could be my true self and appreciated so many of my classmates being open about their beliefs. I did not expect faith based motivations or experiences to be as welcome and celebrated as they were in a place like Harvard.

A few words about Boston/Cambridge. This area had a lot of the same characteristics that we loved about Silicon Valley, the people are similar in a lot of ways. I have always loved meeting interesting people doing interesting things and boy this town is full of them. Especially coming from the Bay Area we were shocked at how clean and safe much of the city was. Having the Charles river run out into the ocean, passing Boston’s beautiful skyline just really makes it one of the most beautiful cities in America. We loved the history, architecture and quirks about Boston. I never had class on Fridays during my whole program and we went on so many weekend trips to Maine, Vermont, Rhode Island and NYC. As New England newbies we loved our crash course in the culture, food and all this area had to offer. Even with our aggressive weekender schedule, it feels like we only scratched the surface. 

The cold is no joke and we are not cold weather people. I think the best thing we did was have covered parking and geared up. We spent a small fortune at the local Patagonia store, but it was worth it. We had never experienced a winter like that, but between the gear and a few well planned vacations to warmer destinations it really was not that bad. In some ways this past year felt like a gap year for the whole family. We are not staying in Boston, but I think Boston will probably forever be a very special city for our family because of this experience.

I’ve always highly valued new experiences, travel, adventures and learning. In that way, this program was tailor made for me. I think the value of graduate school often comes down to what you were expecting, which can vary widely between folks, but for me, this program met and exceeded my expectations. I felt like I was able to meet all of the goals that I had outlined at the beginning of the year. Going back to school was not only a career based decision for me, it was a mix of career, personal interests, my belief in life long learning and for fun.

If you're reading this and thinking of going back to school, I have a bit of advice. The first is to really think about what you would want to get out of graduate school. Especially later in your career, the opportunity cost can be very high but your ability to focus and make the most of the experience is in some ways more optimal a bit further down the career road. I also think you should shoot for the stars. I’m grateful for some friends and mentors that always encouraged me to shoot higher than maybe I thought was possible. If there is no one in your life like that, give me a call and I’ll be happy to pay it forward and give you a pep talk.

If you're thinking about this program, the best advice that I’d have for you is to tell a strong and compelling story about why you, why now and what this program will enable you to do. If you look at each class you can see the admission’s committee’s methodical approach to make a diverse (in many dimensions) class. Almost no one is that similar, so be your authentic self and tell your story clearly.

If you actually read this whole blog post, at this point you might be very disappointed to realize that I’m not going to talk about what is next for me career wise. At the time of writing this post, some things are still in process, but once they are finalized I’m definitely going to share in another way too long of a blog post about how the past year has evolved my career thinking and why I’m doing what I’m doing next, so stay tuned!