Should I go to College?

At the end of this post there is a poll. It asks, “Should I go to college?” If you have a moment, please answer either yes or no. Thank you.

This August will be the first August that I am not going to school. At 20 years old I have never lived through a fall semester without going to mandatory classes of some sort.

I am an outlier. Nearly all of my peers are enrolled in either a two or four year university. Most everyone I know is ecstatic about returning to campus in the coming weeks.

Working full-time, commuting, and taking on more responsibility has made me feel older, wiser, and more experienced.

But, at what cost?

8 months have gone by since my decision to leave the University of Pittsburgh. I think now is a good time to reassess my situation and determine if I should plan a return back to school in the near future.

About me

I am going to tell you a little about myself and where I am currently at in my life. I am going to tell you where I want to go, where I want to be, and who I want to become. Please let me know if going to college would be beneficial on this journey.


  • I am 20 years old.
  • I am a white man.
  • I have completed some college with no degree.
  • I am single.
  • I am employed.


  • I scored a 1900 on my Scholastic Aptitude Test (SAT).
  • I achieved a high school GPA of 3.6.
  • I enrolled in 10 Advanced Placement (AP) courses.
  • I was accepted to DePaul University, NorthEastern University, Drexel University, and the University of Pittsburgh. I did not get accepted to Villanova University.
  • I attended the University of Pittsburgh and had a GPA of 3.1.
  • I have 51 college credits.



Currently I work at a start-up company outside of Washington, D.C. My business card says, “web developer” on it. I write a lot of code, I learn a lot of best practices, and I dabble in design.

The CEO has a passion for teaching others. He mentors me. I have had one on one conversations with him about start-up financing, how to hire the right people, and how to build process. He has a passion for educating, and I am always a welcome audience. I am learning a lot from him.

The lead web developer has taught me how to be a professional. He has helped me learn to “slow down”, be more organized, and think more.

I work in an open office. I learn a lot from everyone – account managers, sales people, everyone.


I recently did an in depth goal setting session. I have outlined goals for the next three years of my life. Those goals align with who I want to be, where I want to be, and what I want to be doing in the future.

In the future I want to be in business. (In the present I want to be in business.) In the future I want to collaborate with others. I want to continue learning new things. I want to be fundamental in building something that is useful, effective, and provides value.

I know I am passionate for a lot of things. I want a shallow knowledge of a breadth of topics, with a deeper knowledge in only a few.

With this information in mind, should I go to college?

YC Fellowship Application – Future Employee Benefits

Y Combinator announced the YC fellowship program earlier this week.

YC Fellows will receive a $12,000 grant and advice from the YC community for 8 weeks (from mid-September to mid-November) to go from an idea to a startup. Fellows need an idea or a prototype and the ability to work on this full-time for 8 weeks.

If you are unfamiliar, Y Combinator is a seed investment firm targeting startup companies. The combined market capitalization of all the firms YC has invested in is over $30B.

I have replicated the YC fellowship application questions here on my blog. (Keep in mind there are 120 word limits on every question.) Below are my answers where I outline a company called Assure.

What is your company going to make?

This company provides benefits to employees of the sharing economy.

Independent contractors miss out of the benefits that come with full-time employment. Assure changes this.

Assure bridges the gap between full-time employee and independent contractor. Assure provides retirement contributions, medical insurance, and general liability insurance to members of the sharing economy.

In two sentences, say the most impressive thing about this team / startup.

I want to do something important. I want to create something of value.

Please tell us in one or two sentences about the most impressive thing that each founder has built or achieved.

I dropped out of college when my mom was diagnosed with lung cancer. A month later I was hired full-time as a web developer with skills I taught myself.

Why did you pick this idea to work on? Do you have domain expertise in this area? How do you know people need what you’re making?

A lot of my peers are oblivious to the benefits that come from being a full-time employee. (Something I have learned only recently after being hired full-time). Retirement contributions (401k), medical/dental insurance, and general liability insurance are the three areas I have a touch of experience in.

The sharing economy is expanding. A large number of jobs are tied to this industry. That number will continue rising.

Assure provides the safety and security employees need to maintain the growth of the peer to peer sector.

What’s new about what you’re making? What substitutes do people resort to because it doesn’t exist yet (or they don’t know about it)?

Providing benefits to employees who are independent contractors is not new.

Currently a contractor at Uber has scattered benefits. They have an IRA for retirement savings. Then, general liability insurance to protect their interests while working. And finally medical and dental insurance from their parents.

Assure brings these three interests together. Contractors wish to legitimize their employment. They will turn to Assure when they want their retirement contributions matched. When they want more protective liability insurance. Or when they turn 27 and no longer qualify for their parents medical coverage.

Who are your competitors, and what do you understand about your business that other companies in it just don’t get?

Companies that hire full-time employees are competitors. As are insurance companies that cover individuals.

Companies that hire full-time employees limit potential customers. While Insurance companies provide similar coverage to what we offer.

Our competitors are too slow to adapt to the sharing economy. Assure is agile enough to adapt as the peer to peer employment market grows.

How will you get users? How do or will you make money? How does this become a giant company?

Assure must educate people to turn them into users. Assure must provide information that allows millennials to see the value of working in a sharing economy while also receiving traditional full-time benefits. There is a knowledge gap.

Assure collects monthly premiums from members. Premiums are aggregated and invested. Profit is made from investment income, not premiums.

Assure is a component of the sharing economy. Employment opportunities are changing. Workers in this new economy will want benefits, Assure makes sure that happens.

Applications for the YC Fellowship are due by Monday, July 27th, two days from the time this post was published.

If you have feedback, please share it. I would appreciate hearing it before I press the submit button on Monday!

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My 3 Year Personal Growth Strategy

Last week I outlined a strategy for writing down goals. This week I am sharing my 3 year, 1 year, and 90 day goals, as well as my strategic road-map to get there.

If you have never written down your goals before you should.

A mentor of mine reached out after reading last week’s post and reaffirmed the importance of goal setting.

If you are serious about achieving your objectives it is imperative that you take the time to write out a plan.

3 Year Goals

  1. I oversee operations of the technical department at my current employer. I manage, teach, and help new employees get on-boarded and integrated in our processes.
  2. I maintain an open source web application with an active and happy user base. I create a platform where others can make an impact on the web.
  3. I own a duplex. I live in one of the apartments, I rent out the other for supplemental income.
  4. I teach a course at General Assembly and participate in local MeetUp’s on the weekends. I am active in my field and help others learn skills that I have mastered.

1 Year Goals

  1. I work directly with the marketing department to create an industry benchmark report. I have a good knowledge of data analysis software such as Pentaho, Mondrian, Saiku, and Hadoop. I help teach other employees how to use these software.
  2. I receive positive feedback and initial traction for my online web application. The start of a community is evident and others have begun contributing to the project I started.
  3. I live at home, and I save my money. I invest passively through an IRA account and maintain a long-term time horizon. I have a credit card and have started building a credit reputation.
  4. I participate in a local MeetUp, and have connections with a few of the organizers. I have built a small network of resources that I can interact with.

90 Day Goals

  1. I improve process for our production department. I contribute with other developers to create protocols and guidelines for code development, testing, and deployment. I have written the first draft of what will become a guidebook for new employees.
  2. I have written a business plan. I have mapped out what I would like to build, how I would like it to grow, and who I want to be involved. I calculate every step I need to take to create a successful web application.
  3. I transfer funds that I am currently actively managing into a more passive account. I have my direct deposit automatically contribute to my long-term investment account.
  4. I help teach interested friends and family how to write code. I work with a few people on the weekends to teach them the basics of front-end development.

The Goals

The list above is the result of visualizing where I want to be 3 years from now, 1 year from now, and 90 days from now. Each goal from the 3 year section correlates with a goal in the 1 year section, and each 1 year goal correlates with a 90 day goal. The overarching goals could be labeled as;

  1. Career advancement
  2. Open source application
  3. Real estate
  4. Teaching.

After this visualization process I wrote out why I wanted to achieve these four goals, and how I would know when I have achieved them.

Career Advancement

I want more responsibility, I want to learn by doing. This goal is intended to help me learn the in’s and out’s of managing others and hiring new employees. I want to take this experience and use it to help me when I start my own company. I want to advance my career over the next 3 years in an attempt to learn as much as I can before launching my own venture.

This goal will be fairly obvious to realize. As the company I currently work at grows, members from the initial team will take on more responsibility. I want to be a  part of this expansion. I will accumulate a wealth of knowledge, and actively share it.

Open Source Application

I want to create something that others find valuable. By creating an open source project I will be giving other people an opportunity to join a community of like-minded individuals. By engaging with people who have similar interests I will grow my network and build my personal brand.

This goal will be realized the day that other members of the community maintain the project. The moment where I am no longer the individual tasked with maintaining the application will be the day that I know users are happy and engaged. I want to spur the creation of something that others find immense value in.

Real Estate

I want to save my money. I want to retire when I am young. Buying real estate is a strategic investment for the future. I intend to live in the first property I buy, and with the purchase of a duplex I will have an opportunity to diversify revenue streams. I will also learn rather quickly how interested I am in becoming a landlord.

This is another goal that will be obvious to know when I have achieved. The day that I sign my mortgage and have a set of keys in my hand will be the day that this goal is realized.


I get great personal satisfaction from helping others. Teaching a topic or skill requires mastery of the topic. By helping others I will be getting personal satisfaction as well as further mastery of topics I enjoy.

I will have met this goal when someone I have helped mentor has created or done something they are proud of. My teaching and mentor-ship will have played a role in their success.

Steps to Take

To achieve the above goals I will need to lay out distinct and actionable steps to take. This is the final aspect of a goal setting session, after completing this section you will have a road-map that you can begin to follow. If you struggle with creating these steps, remember that you can always add or subtract a step from your plan. This is a fluid document that you are creating.

Career Advancement

Steps required for achievement Deadline for each step
Master and innovate upon existing processes at work. 90 days
Create and implement new processes that help improve productivity and reduce costs. 1 year
Further gain the respect and trust of my peers and coworkers. 1 year

Open Source Application

Steps required for achievement Deadline for each step
Conduct market research and narrow down the possible application ideas. 90 days
Search for others who are working on similar projects or who share a similar vision. 1 year
Reach out to my network and actively share what I have been working on. 1 year

Real Estate

Steps required for achievement Deadline for each step
Don’t wastefully spend money. Immediately
Save and invest my money passively. Immediately


Steps required for achievement Deadline for each step
Meet up with peers that share similar interests in programming and development. 90 days
Learn and be aware of the foundations of Computer Science 1 year
Master HTML and CSS, the dive deeper into JavaScript, and JavaScript framework. 2 years

What Happens Next?

Obviously I have a lot of work to do.

I have already gotten started on a few of the objectives I laid out above. Now, and over the course of the next 90 days is the time to buckle down and hit some of my milestones.

Please feel free to mimic the content above. This strategy has helped me immensely, and I hope you can use what I have written as a model to create your own plan.

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