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I Thank My Lucky Stars for College Works...

Payroll Guest Speaker 2019

I read this post on LinkedIn and thought that Justin Welsh, the SVP of Sales at a Santa Monica based tech startup, did a perfect job explaining what happens when you get the opportunity to work somewhere extreme early in your career. He describes how I feel about College Works Painting.

I always compare the College Works intern experience to an "entrepreneurial bootcamp." You go from zero (an inexperienced college student) to running a profitable 5-6-figure house painting company in 6 months. You're pushed far out of your comfort zone, and it requires a massive amount of hard work and resilience to succeed. 6 months can feel like 6 years. More than half of all the interns that start don't make it to the end.

But the ones who thrive? They become founders and CEOs (like Omar and Taylor), VPs and Managers, company MVPs and top performers, sometimes making well over 200k IN THEIR TWENTIES. And best of all, this "tribe of intense lunatics" we call the #CWPmafia are lifelong friends who celebrate and support each others through their lives and careers.

Everything else will be cake...

For the current CWP interns of 2019, you are still in the trenches, working long tiring days and working through endless stressful problems. As you approach the final stretch of the summer, try to keep the big picture in mind. It'll all be worth it in the end.

You might not see it now, but eventually, maybe 2 or 5 or 10 years later, you'll get it. You'll eventually look back on that insane summer painting houses, and smile. And whatever you do after this, I promise you it'll be cake in comparison.


I had no clue what I wanted to do in college. I switched majors from Journalism, to Humanities and Arts, to Economics. Just by looking at me, you could tell that I mostly just wanted to surf and party and delay real life for a long as possible.

My senior year, I was presented with the opportunity to do CWP, but was unsure if I wanted to do it. It seemed like a lot of hard work, and I knew absolutely nothing about running a business.

Brian and Mike saw a lot of potential in me, and knew exactly how to recruit me...

"Imagine that your business is making you money while you're at the beach surfing."

There was something that clicked for me in that moment. It was like I was presented with an escape plan out of the traditional 9-5 career path, which I always thought wasn't really for me. So I jumped in, full commitment to this whole entrepreneurship thing.

My intern experience was a roller coaster, as any alumni knows. I fought to be a top intern, and I cared deeply about doing a great job for my clients, but I also never lost sight of the vision of getting my business to the point where it could run profitably and smoothly without me being there. I went through lots of stressful projects, shitty employees and learning lessons, but I eventually got there, with 4 amazing employees that I trusted to start their own job sites in the morning while I surfed. This experience changed my whole perspective on my future career.

What I would also learn over the next several years is that when you perform highly, breakout opportunities get presented to you.

I became a District Manager because I thought, if I learned and grew so much intern year, imagine how much I would learn and grow through a DM year. Plus, I really liked the people and the culture and knew there was something special here.

Then I got presented the opportunity to move to Norcal and help expand the business there. It was a risky and scary decision, and after my mom telling me that this was a "character-defining decision," there was no way I could wimp out. On paper, my rookie DM year looked unremarkable, 300k in revenue and I didn't really make any money after factoring in the cost of driving to my interns spread between Redding, San Jose, El Dorado Hills, and Modesto. But what the numbers don't show are the nights I spent sleeping on the living room floor lined up like sardines with my expansion team, the nights I slept on my air mattress in my furniture-less apartment, and the nights I spent sleeping in my car pulled over somewhere between Chico and Concord too tired to make it all the way home. We worked so hard and the whole team had an intense make-it-happen attitude. Over the next few years the Norcal division would produce some of the highest revenues and most successful alumni in the history of College Works.

Then a few years later I was presented with the opportunity to take over the business from Brian. Being an owner and the operational leader of the company was another huge step for me, that required a lot more personal growth. My success as a DM came from my ability to lead from the front, perform highly, build relationships, and be the cool boss. But now I would need to grow into a more mature leader, earn respect, learn to inspire others, and be a role model.

Derek and I ran the company for 4 years, from 2014-2017. Our vision was to create a training program for college students that was so good, that hiring managers in California, especially Silicon Valley, couldn't ignore the caliber of our alumni. By some objective standards, and mostly subjective ones, we created incredible momentum towards that vision. Not only did internal hiring managers at companies like Google take notice, but so did some Silicon Valley recruiting agencies, one of which being TheLions.

In total, I spent 10 years with College Works, a decade, so crazy, what a wild ride.

Leaving CWP was like...

The timing to move on seemed right. We had 2 solid successors in Rob and Pilar, so the company would be in great hands. And my stepdad was retiring and wanted to sell his small business to my brother and me.

Actually it was like...

The year after leaving CWP I call my Year of Failure. It was a big leap into the unknown, and I definitely didn't make a smooth landing.

I wrote about my failures in another blog post last year, Boxing With Failure, but here are the cliff notes.

  1. The opportunity to take over my stepdad's koi fish products business was great but not really for me, and eventually he ended up selling it to different buyers. So there I was, starting my career adventure back at square one.
  2. My brother runs a successful e-commerce business through Amazon FBA, so I decided to follow in his footsteps. I invested nearly 20k in inventory and freight forwarding expenses. To make a long story short, I made a bunch of bad decisions and broke some of my own rules, and paid the price. The business failed and I lost nearly 20k in the process.
  3. Part of my risky moves were made because I had a healthy portfolio of cryptocurrency investments that I saw as a potential safety net. But by the time everything went down, crypto had crashed. I was now back in debt and with no income.
  4. Now I needed to make money, so I entertained the idea of getting a real job. A CWP alum reached out to me on LinkedIn telling me about HealthIQ, a startup in SD that celebrates the health-conscious by negotiating lower rates on life and health insurance. Very cool concept, but after shadowing their inside sales reps selling life insurance I really thought twice about getting a real job, and declined their offer. 
  5. I was recommitted to go the entrepreneurial route once again. Johnny Rhee, one of my favorite leaders and mentors at College Works, asked me to do some sales for his solar company on the weekends. After going through research and training on solar, I told Johnny I was interested in starting my own solar sales company. To make another long story short, I spent a few weeks going door-to-door trying to generate leads, and got my ass handed to me.
  6. I was now even more in debt and went back to job searching with my tail between my legs. I found a remote Account Executive role with Liftopia, selling SaaS for ski resorts and waterparks. It seemed like the perfect role for me, they loved my profile, and flew me up to SF for a final in-person interview. I thought for sure I was going to get the job, but they ended up giving it to a referral who had more industry experience than me.
  7. Finally, in frantic desperation at this point, I sign up for Nutrition School. I thought it could maybe provide a new career path, though the high upfront tuition cost only made my money and debt problems worse. I had 30k in debt and no job, but least I had something to work towards. 

I'm not going to lie, this was a tough time and I started to doubt myself. I thought, maybe with College Works I got lucky, maybe I'm not really as smart and capable as I thought I was, maybe I don't have what it takes to be an entrepreneur. But despite the negative thoughts, I would always move on to the next opportunity quickly.

The next opportunity I pursued was with TheLions, a recruiting agency that recruits sales people for tech startups. I always thought that this could be a good fit for me, but my ex-girlfriend works there and honestly I was scared to ask her. Once we talked, she told me they had a perfect role for me, called their "OG" role, which is kind of like starting up a Lions franchise in an "other geography" outside of SF. It's a fully remote commission-only role, and with no base salary it would be at least another couple of months until I started making money and could start digging myself out of debt. Seemed risky, but also seemed perfect for me. Would I trade a guaranteed salary and benefits for the ability to be my own boss and not be managed by anyone? 100%.

I just passed the 1 year mark with TheLions and I love what I do just as much as I loved College Works. I was able to pay off my debt 8 months earlier than I expected, and I'm saving and investing again. As my own boss, I have the freedom to go on midweek surf and snowboard trips, and train for Ironman and ultramarathons for several hours per day. I'm honestly living the dream! I feel lucky to be in this position, but obviously I went through a lot to get here.

"Entrepreneurship is not just about starting companies, it's an approach to life."

Through College Works I learned that I wanted to be an entrepreneur, but what even is an entrepreneur?

Entrepreneurship is about having a vision, and committing to make it happen.

My vision is freedom, to escape the 9-5, where no one can tell me what to do, where to be, what time I need to show up, what to wear. To be able to surf at 10am on a Tuesday if the waves are good.

Your vision might be different - security, luxury, family, impact. Maybe you have a dream company and/or a dream life in mind.

There are many different versions of entrepreneurs. There are the Steve Jobs and Elon Musks of the world, who run companies at massive scale, make products that change the world, and try to solve the world's biggest problems. Then there is Tony Hsieh (Zappos) and Blake Mycosckie (TOMS) who both ran shoe companies, but to them it's hardly about the shoes, it's about the company culture or the social impact. My favorite entrepreneur is Yvon Chouinard of Patagonia, a dirtbag surfer and climber who became an accidental businessman and now runs a company whose mission it is to not only to fight for the environment but to also be a model for other businesses to follow.

I also learned about lifestyle entrepreneurs, who run businesses not just designed to serve their customers but to also support their own lifestyle goals. The 4-Hour Workweek by Tim Ferriss was a very influential book, where I learned about soloprenerus and micropreneurs and digital nomads.

Artists and writers can be entrepreneurs. Freelancers and independent contractors are basically entrepreneurs. An intrapreneur is someone who runs a "startup" within a larger organization.

Anyone can bring an entrepreneurial approach to their careers, and in The Startup of You, Reid Hoffman (Founder of LinkedIn) argues that you should. He says that you should approach your career like it's a startup and invest in yourself, develop competitive advantages, and take intelligent risks.

One of his main concepts is the Permanent-Beta Mindset - you are a work in progress, therefore always be investing in yourself. You do this by constantly building career capital - skills, knowledge, relationships and connections.

Career Advice: Old School vs New School

Old school advice says figure out where you want to be in 10 years, and come up with a plan for that. Careers used to be kind of like tunnels - you’d decide on a career after college, and work there until retirement, a very linear path. This makes choosing the "right" career path in college very important and scary.

New school advice says that planning is overrated, and it's more important to be flexible, and able to adapt. Plus, how can a college student really decide on a career path with such limited knowledge of all the potential careers out there, and without much real feedback on what they are good at or what kind of working conditions they thrive best in?

Startups learn through beta-versions and minimum viable products (MVP). It's a learning-by-doing model, launch before you're ready versus waiting for perfection, obtain feedback from real customers, then iterate. Learning is prioritized over profits early on. Careers should be the same, you can really only learn from doing, gaining experience in the real world. College Works is a great example of starting before you're ready and learning on the fly.

Sure, having a vision, an ideal scenario, a plan A, or at least a general direction is important. But also realize that through experience and learning, your vision will evolve, your plans will improve, and your direction will change. Embrace that, be flexible, take detours.

Job fit, or how much a certain job (industry, company, mission, product, people, working conditions, day-to-day responsibility, growth potential, etc) is suited for you, should be of the highest priority as you build a career. But you really only discover job fit through experience, and it evolves over time as you grow and evolve. I wrote a post called Career Moves where I talk more about making career decisions.

Pursue Breakout Opportunities

The trajectories of remarkable careers are not slow and steady and up to the right. Rather, they are marked by breakout opportunities—career turns or experiences that lead to unusual rapid gains.

The College Works internship is a great example of a breakout opportunity - a short 6-month experience that leads to unusual rapid gains. For me, becoming a DM, moving to Norcal, and becoming a VP/Partner were also breakout opportunities in my career.

As Justin Welsh said in his LinkedIn post, you probably won't find a breakout opportunity at some "business as usual" company. Breakout opportunities can come in many shapes and sizes, maybe you find yourself taking a pay cut to join a scrappy mission-driven team, or going to work at that top-tier company where you are surrounded by the best-of-the-best people, or going with that early stage startup where your role is less-defined and you get to wear many different hats, or starting that new business venture with a co-founder.

Opportunities arise in a very serendipitous way. If I was 5 minutes earlier or later to that Econ class, I might have never found College Works. I might have never arrived at TheLions, or at least with the gratitude and perspective that I have now, if not for going through each of the individual failures on my failure list post-CWP. I can't ignore the amount of luck and randomness that has shaped my career.

Opportunities come at random, but you have a choice to pursue them, and with what level of commitment. Sieze opportunities, don’t let fear or complacency get in the way.

Stir the Pot

To increase the likelihood of these breakout opportunities, you need to take action. Be in motion and court selective randomness, meaning, when you do something, you stir the pot and increase the odds that seemingly random ideas, people, and places will collide and form new combinations and opportunities.

One of my favorite quotes of all-time is, “The harder I work, the luckier I get.” When you work hard, it seems like you are getting luckier, with more opportunities arising, but the work hard is highly correlated.

Closing Thought

As you finish your intern year of College Works, see it not as the end but rather the beginning. You can take another step forward, or take a step back. You can take a break (which is tempting), or you can keep stirring the pot. Remember inertia, objects in motion stay in motion, objects at rest stay at rest. Use the power of momentum into your next opportunity.

Anyone who has the opportunity to take a DM promotion should seriously consider it, as it's 10x the learning and growth of intern year.

Either way, I want to encourage everyone to work hard through their twenties. If you look at your career as a startup, then your twenties are launch mode, which means it's the time to grind. The skills, habits, traits, and connections that you build in your twenties will pay off exponentially later in life.

My career story is one of chance and choice, serendipity and hard work, successes and failures. If there is anything you learn through my story, it's to have a vision and commit to making it happen, to not be afraid to fail, and if you work hard, magic happens.

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