Why I'm an Upstart

I've officially been an Upstart for 2 weeks and I couldn't be happier with the decision...though I could have a few more backers! It's great to be part of a platform where the start-up behind it just raised a round of funding and is on a roll. Like anything new there are plenty of detractors who don't quite grasp its significance. That's to be expected with any new idea especially one so personal. The MIT tech review looks at it as just a popularity contest to be one by those who market themselves well. Isn't that the case with most startup financing? I've heard others ask, "how is this any better than investing in that person's company?" Here's one of my most recent responses which really emphasizes why I personally chose to become an Upstart:

The primary reason I joined Upstart is because I would otherwise lack the resources necessary to pursue a business for you to invest. Liabilities from college loans, living expenses, etc have never allowed me to focus on my goal of building a business over getting a paycheck. Even the consulting work I'm doing now is a distraction from focusing my efforts on learning to code, building a MVP, and ultimately a team. Upstart will empower me to achieve these goals by eliminating most of my liabilities. It will also reduce the pressures of trying to raise funding for an idea rather than a product. Above all else it's a great opportunity to gain mentors who are investing in my success rather than just another seed round. Making it personal should feel awkward but it should also foster a deeper connection than is possible with a convertible note in a Delaware C-corp.  

It took me awhile to get over the awkwardness and to feel comfortable with the model. It also took some convincing from one of their original backers. By no means is it better for everyone but at this time it is for me. 

It really isn't for everybody. It is for someone who wants to pursue a dream but is saddled with college debt...this guy and most of my generation. My plan for the money is to pay off as much of my loans and credit card debt as possible. Better to pay of those high interest loans with this low interest money and hopefully get some great backers/mentors in the process!

What do you think about this new model? Popularity contest? Modern servitude? Brilliant?  

I know I love Boston but Burlington is my home.

Ironic? Hypocritical? Confusing? I know. A day after professing my love and commitment to Boston I follow up with a post on Burlington. Burlington is where I grew-up and it's where I hope to return someday but not yet. While becoming a member of the community here I'm also trying to help influence the tech community in Burlington. Our vision, I can say our for this project, is that Burlington can become a hub for tech just like Boulder. Brad Feld wrote the book on how to accomplish this feat but we're all about reinventing the wheel. My ultimate goal is to help build up Burlington so that when I return it's better than I last left it.

Our project is called the Burlington Code Factory and it's part of the Vermont Venture Foundry (I know...not very original). This is our first step in building the community and here is the email we're sending to VT's current tech leaders:

First let me thank you for your leadership and interest in advancing the creative economy in VT. Now let me get you to hear what a group of us are doing to take Burlington from what it is and to transform it into what it could be. 

We all know there is much work to be done in improving the technology community and efforts are underway to attract more developers to VT. We have the natural resources and access to big markets but something is missing to attract and retain great talent. Many place blame on the academic institutions, some to the lack of funding, while we choose to point the fingers at ourselves. No one is going to snap their fingers and instantly attract people who think in binary. 

We need to do a better job of fostering new ideas, supporting budding entrepreneurs, and growing from 2 big private tech companies to dozens of thriving small-mid size startups. We need the world to know that you can come to Burlington and raise a seed round, A round, and B round w/o having to relocate to SV, Boston, or NY. We need to have more meetups, more hackathons, and more social settings if the world is going to sense a community here. We need to bring what happens in the shadows into the public so that the tech community understands VT is a hub as strong Boulder. 

In order to get there we must start somewhere. Today we are launching the Burlington Code Factory for New England based CS undergrads. Interns will receive a competitive stipend to live in Burlington and join several startup projects which already have prototypes (frameworks) and vetted business models. Each intern will have the opportunity to become a co-founder and ultimately receive equity in the project. This effort is our first step in getting those couple dozen startups. If we can change the misconception that you have to go to Boston or NYC or SV with the younger generation older developers will follow. As the pool of young talent grows so will the community. 

Help support this effort! Share the attached promotional materials and link with your colleagues, universities, and prospective coders. Offer to be mentors, advisers, backers, etc. 

Looking forward to fielding your questions, comments, support. 

All the best,

The Team at Vermont Venture Foundry

If you know of any aspiring coders who wants to build something cool this summer share the following link with them:

http://venture-foundry.com 

Know of any similar projects, internships, etc? Want to get involved? Comment below!

When life throws your city...

Last week was a difficult one for getting things done. I had no interest in blogging, social media, or even working. The posts I had written seemed incredibly insignificant given everything going on. I still held my scheduled Google HOs, responded to emails, volunteered at Pine St, and even coached my rugby kids out in Waltham. It was just one of those weeks where you reflect on life and have very little interest in interacting with the world. 

It's incredibly difficult to reflect on what we experienced last week here in Boston. It's unfortunately something that happens almost every day in this world but never in my back yard. I had never been to NY before 9/11 which made it seem so foreign even though it was clearly on our home soil. Conversely my wife and I have spent a fair amount of time in Copley Square and even bring visitors on our "This is Boston Tour." I went for a jog at 1:30 on Monday and even considered going to checkout the marathon as I ran along the esplanade and across the Mass Ave bridge. I was also planning to run for charity in this year's marathon until an Achilles injury halted my training. That said, my inability to work was less about what ifs and more about what for.     

The question I keep asking is what am I doing to ensure I maximize my impact for my family, this community, our country, and the planet? What steps should I be taking to do so in my allotted time? It's no secret that death could come at any moment but events such as last Monday are times to absorb all of the anguish and reflect on oneself. Obviously it's also the time to support the victims and community as many did last week and we are all thankful for the support the world showed Boston. 

My wife and I have fully adopted Boston as our home (as much as we can from Cambridge ;). We absolutely love everything about being in this fantastic metro area from the sports teams to the culture. We are giving back to the community and trying to help organize it. We love Boston and will never be afraid to live in it just as I won't be afraid to run in next year's marathon. See you in 2014!

Haters gonna Hate

I recently had an angel friend tell me that I was stuck in selling mode. That I had no real passion for entrepreneurship and that I was simply riding a trend. That I was no different than the banker, consultant, MBA type (he has an MBA) who sees "easy money" and fame. It took everything I had to not say FUCK YOU and walk out of the meeting...that and I hadn't finished my breakfast yet that he was paying for #BootStrappin.

With the exception of this rant I've valued his mentorship, feedback, etc but this is a case where I think he's rushing to judgment. I graduated in January 2010 and immediately resumed my work with Encore Redevelopment where I was the 3rd hire and played a critical role in their pivot to renewable energy, as an intern. This was my first real opportunity to be an entrepreneur other than the small hustles I did throughout High School (Red Sox nation wristbands come to mind). After this I tried to start 2 companies, helped several more, and eventually landed at Zipcar. I quit that job to learn to code, pursue Upstart funding, and ultimately get back in the startup game. I saw it as more of an investment as I now have sales experience and have seen the belly of the corporate beast. All of that said, I'm not sure where the gap is between my messaging and his perceived reality.

The reality is I think by selling he meant I'm talking to much with not enough action. This is a problem I identified awhile ago between my Linkedin title (Aspiring Entrepreneur) and my general use of forward thinking words. I've since stopped and no longer say "I'm hoping to build a company" because the reality is I am. I built a site overnight for my bootstrapping work consulting SMBs with their Macro Inbound Marketing strategy. I went through several iterations of my application for Upstart which I'm hoping launches later today. I'm helping launch an incubator in my hometown and recruiting applicants for those college sophomores/juniors interested in a paid coding internship. Finally - I'm building a team to pursue the first of many ideas I want to build because a team will ultimately get it done faster than I will with my codeacademy training.

The reality is I'm done worrying about how people perceive my abilities. I know what I can do because I'm doing it. If they're too busy, lazy, or ignorant to look at the evidence, that's on them and I can't change it. Note, one thing I am still working on is being less negative when i write...it's just so hard when there are so many people looking to knock or drag you down. That's why they say, Haters gonna Hate. So keep hating! I'll keep building :)

Yet another view on company culture.

Is it just me or is everyone blogging about culture these days? Charlie O, B Horowitz (is that how you spell it?), and Hubspot homeboy Darmesh (sorry about that one, BHorowitz got Izzo stuck in my head). How fitting that I decided to leave Zipcar primarily due to the culture of the company which in my opinion had become destructive. I mentioned it briefly in my moving on post with the intent of expanding on my observations and thoughts on how to build a world class culture. To start, lets state the obvious as expressed by all 4 of these posts (I can include my own, right?):

Beer, food, foosball, swanky office furnishings, flexible working hours, unlimited vacation, yoga, and even daycare are all part of your style as Charlie O puts it. They in no way define your culture. The best companies are people centric and everything else is just frill. A kegerator won't do anything to keep me at the office until 9pm but the people I work with will. I'm not talking about talent management, core competencies, performance reviews, or even NPS people centric. I'm talking about treating employees like they're teammates and not simply labor. Economists look at people as labor. Accountants think of people as expenditures. Managers see people as liabilities. I tell my rugby guys that the best teams act like families and that holds true for a business.

-Courtesy of 3 Geeks and a Law Blog

Flow charts like the one above make great points but they are simply overkill. As my most recent resignation letter quite clearly stated: "After much consideration, I've come to the conclusion that we are no longer following our core values or mission." Could I have been anymore blunt? I was advised to reconsider putting something so strong in text and knew I'd have to back it up. I broke down my thoughts on culture into 3 key features in my exit interview:

1. Communication
2. Passion
3. Drive

All 3 are equally important to building and fostering a corporate culture that brings the best out of your entire team. I can really only speak from my experience at Middlebury but I think college's nail this well. If you look past the bureaucracy of the administration, you'd see a sea of students all able to speak freely to any administrator, teacher, "authority" figure as long as they did so respectfully and with legitimate concerns. Everyone in the community whether they be faculty/staff (management) or students (employees) bleed Blue & White from the hockey arena to their dorm rooms. Finally everyone was so driven to achieve personal success but more importantly to make Middlebury the best place on earth...period. If a 2,500 student academic institution can nail this recipe, why can't a business?

I hope the day comes when a young, up and coming generalist at my third company walks into my space (I will never have an office) and isn't afraid to call me "a fucking asshole" followed by "you are single handedly ruining this company. That's communication, it's passionate, and if backed by data and a plan to fix the mistakes, drive. I would even promote that gentle-lady if the company had positions of authority to be promoted to.

While extreme, this example emphasizes that autonomy and respect are key to building a winning culture. You can't have either without the freedom to express ideas which is the basis of communication. If your teammates can't be frank because they fear retribution then you aren't building the right culture. Hubspot is spot on by being data driven because data provides you with the ability to take an opinion and make it a fact. A culture of finding and expressing truths will foster sharing and innovation rather than squelch it.

You can't have love without passion and you certainly can't be successful without either. Passion for the product or helping your client is fine but you need to find people who eat the dog food (drink the champagne if you will). It can be infuriating to have people say "Obsess About the Member" when they are hardly a member themselves. When you're trying to disrupt transportation and the majority of your employees drive to work in their personal cars every day...you have a problem. I don't see how you can build a productive culture without a passionate team and that's what we do at Brandeis. We weed out the people who aren't fully committed to the team but more importantly the game of rugby. That way we don't have people dragging us down because they don't want to put their body on the line or sacrifice study time for practice. Same has to go for employees (especially management) of a company. If the people leading you into battle aren't truly passionate about the product or lifestyle you're selling, your company is toast.

The final feature is Drive. The drive to be successful and to want to not only win your market but smoke the competition, incumbents and upstarts alike. The drive to always be improving yourself and your processes to squeeze every ounce of efficiency out of your efforts. This comes from being competitive which I'll cover soon in a post about sports and business but more on that later. It's not just competing with the competition as you should feel compelled to push your colleagues to always be the best they can be.

This brings me back to the family analogy. Families must always communicate, they are clearly passionate for each other, and most importantly they always have the will to improve their fortune as a collection rather than as individuals (drive).

What comes of my next venture will be determined by how we decide to build the culture of the team. It starts with the values and traits I set out above but is and always will be a moving target because the team sets the culture.

"My Story" for Upstart...the short version

I'm currently applying to become an Upstart and was frustrated with myself because I couldn't make "my story" concise enough for their standardized application. Also verifying my SAT/ACT scores was a challenge because I took them almost a decade ago and apparently they didn't have electronic records then...both scary thoughts. Here is the short version of "my story" as I'm still working on the long one and a Ken Burns style documentary:

I grew up in Winooski, VT in a home with my mom, younger brother, and maternal grandparents. My mom went back to school so we relied on credit cards, student loans, and government programs in my early years. I am a product of the Winooski Public School system from K-12. Going to a school where the majority of kids receive free and reduced lunch can sometimes limit your potential unless you know how to find opportunities. I excelled in academics and athletics while pushing myself to take classes at night including forensic science, public speaking, and even scuba diving. I wanted to be a Dr so I took Biology courses at UVM and CCV all while being the captain of the football, basketball, and baseball teams.

I earned my way into Middlebury College and spent 4 years "discovering myself," still working on it. I switched to rugby, won 2 national championships, helped raise thousands of dollars, and captained the club. Mentorship has always been a part of my life so I was a First Year Counselor, Guardian ad Litem, and Foundation for Excellent schools mentor. I took full advantage of the Liberal Arts even though Economics, specifically econometrics, was what I gravitated towards the most. Posing questions about our environments and using data to discover plausible answers is a powerful way to see the world. Geographic Information Systems was by far my favorite class as data structures are fascinating and topo maps can be breathtaking.

I knew I wanted to get into startups and renewable energy so I faked my way into my first job at Encore Redevelopment. I helped them pivot from having renewable energy be a phrase on their website to being the core of their business. I walked away after 2 years because I wasn't getting equity and thought it was time to start my own thing. Spent time helping startups (getting fired quickly from one) and eventually landed a "corporate" job at Zipcar. I love the product (still a proud Zipster!) but hated the business and left after a year. It was great experience to be a part of a public company going through an acquisition. Now I have a better understanding of how to make one more efficient and look forward to sharing my thoughts with the world. It's time again to find my own way and that's what being an Upstart will help me do.

I'm the type of guy who would rather figure something out then be given a set of instructions and told what to do. I'm tired of sitting on the sidelines and have acquired the skills, knowledge, and ability to attack big problems. I'm a team builder and need to put my experiences learned on the rugby pitch to work in the marketplace. I just need the financial flexibility to chase my dreams without being shackled by college debt.