July 13

Virtual Training Camp Diaries: Michael Montgomery

Week 1 of Training Camp has ended. I have a lot of feelings at this moment. To understand them though, I need to give some context on where they come from. For my journey to this moment has been a long one, hard fought, and arduous.

Having interned for VFA in 2016 I had the luxury of attending an in-person Training Camp. So I had expectations. When I heard that Training Camp would be virtual I was worried. To me, the greatest value of VFA is the community and the people. I was worried that I wouldn’t be able to meet as many people or form real connections with them. I was worried that training wouldn’t be as involved or interesting in a virtual format. I was worried that it wouldn’t give me the same feelings that I had in 2016.

My worries were rooted in my previous experience. An experience that sold me on VFA, and inspired me to be a part of this community. When I applied to VFA I had just been introduced to entrepreneurship. I had heard the word before but didn’t really know what it meant until my Intro to Entrepreneurship class in college. After that, I was hooked. I couldn’t get the idea that this was what I was meant to do out of my head. So I looked for internships where I could get some experience at a start-up and see entrepreneurship first hand. I ended up applying for VFA.

Once accepted, I had a conversation with myself. I recognized the value of this opportunity and I was not going to let it go to waste. I was going to work harder than I ever had before, and learn as much as I could during this internship. I was taking 2 summer classes, accounting and marketing, but I was confident I could still be a great intern.

I set off to Brown University for TC2K16 with the Team and the Fellows. I was immediately infatuated by the whole shindig. The guests who came in for training were amazing. Their trainings were real and valuable. Most of all though, the Fellows and the Team were some of the best people I had ever met. There was this aura of possibility and belief in the future that was intoxicating and infectious. I noticed myself believing more in my abilities. I was coming up with more ideas. I challenged my beliefs, learned new perspectives and grew. I met some of the smartest, hard-working, and amazing people I have ever met, and who I still talk to today.

At the end of Training Camp I felt that I had accomplished my goal. That I had worked harder than I had ever worked before, and that the Team and the Fellows valued me and the work I did. I knew that entrepreneurship was what I wanted to do, and that VFA was the way I wanted to do it. I wanted to be a part of this community because it inspired me to be a better version of myself. It felt like home to me.

Fast forward 2 years and I am a senior in college approaching graduation. I applied to the Fellowship class of 2018 with maximum confidence, borderline hubris, and expected nothing but the best. I thought, “the VFA Team has seen how hard I work and that I can contribute value to a team. They have seen me at my best. I’m sure they will want me to be a part of this community.” I rushed through the application process. Wrote my essays in a couple hours and submitted it. I sat back and waited for the next step.

About a week or two later I got an email from the Team. It said that my application to the Fellowship had been denied. My stomach dropped to my toes as I read that line. Sitting in the living room of my off-campus house with my roommates all talking and having a good time, suddenly everything was quite. My eyes were fixed on that one word, “denied.” As my brain ctrl + alt + delete rebooted, a wave of existential dread washed over me.

I had no idea what I was going to do. For the next few days I crumbled. I skipped classes. I didn’t see any friends. I sat thinking about the future, and what I was going to do in my life.

This had been the one thing in my life to that point that I really wanted. I wanted it so bad I could feel it in my bones. I felt like I had earned my spot in the Fellowship already, and being a part of the community was one of the few things that truly mattered to me. Yet, they didn’t want me. And if they had seen me at my best, working my hardest, and they still didn’t want me to be in their organization, then who would…? If this was the one thing I felt I truly wanted and I couldn’t do it, what could I do? It felt like I had finally found my home, only to be told that I wasn’t wanted there. It was the first real failure of my life, and it crushed me.

After about a week of sulking and self-destructive behavior, I went for a walk. It was a beautiful spring evening in Bloomington, IN. As I walked around the campus, I reflected on the past 2 years. I asked myself, “have I really been working hard for this? Have I given my all to be a part of this community that I treasured so dearly? Is this really what I want?” When I was truly honest with myself, I knew that I hadn’t worked as hard as I could. That I had assumed I would be welcomed into the Fellowship with open arms, and because of that I hadn’t been working to do everything I could to make sure I would be a prime start-up employee. That I had been over-confident in my abilities instead of working to strengthen and master my skills. I knew I could have and should have done more. But I knew that I did really want this. I still had that feeling that I was meant to be a VFA Fellow. I knew I still wanted to be a part of the VFA community. So I asked myself, “if this is what I want, will I let this be the end? Is there anything I can do to still be a part of this community?”

In that moment I knew that this would not be the end. I remembered that you can still be in the Fellowship 2 years after you graduate. I trusted the VFA Team, and if they thought I wasn’t ready for the Fellowship then I trusted that decision. So I went back and reached out to the team for some feedback. The next week I got on a call and listened to the reasons my application was denied. There were 2 main points, the first being that my essays made it seem like I loved VFA more than aligned with the mission of the Fellowship. The second was that they felt that my resume at that moment would make it tough for me to find a position during match.

So I thought about this some more. I asked myself, “do I really want to be a Fellow? Do I just love VFA and the Team? Or do I actually align with the mission and believe in the goals of the Fellowship?” I knew that the Team was not the only thing I loved about VFA. I knew I aligned with the mission. I knew I was willing to work to prove it, and to show them that I was serious. So I thought about what I could do to become a better start-up employee. Sales was something people had always told me I should do, and that it was an incredibly valuable business skill. So I figured I would get a sales job and work for 2 years. During those 2 years I would learn as much as I could about sales and business. After 2 years of hard work and learning as much as I could I would re-apply for the Fellowship.

So I set out to do just that. I got a sales job at Schneider Transportation. I worked hard there for 2 years. I studied sales books, read sales blogs, and learned as much as I could about the business and industry I had chosen to work in. And I found success. I was good at my job, and I liked sales. But I didn’t love the industry and I knew this was only a stepping stone. The Fellowship was always in the back of my mind. After 2 years I was ready to move on, and one day on LinkedIn I saw a post from VFA, “the 2021 Fellowship application is now open.” My eyes lit up. I was ready. I had worked, and sacrificed for 2 years all for this moment. Now I was ready.

Here I am now, writing my Week 1 Training Camp diary. And this journey is what I am looking back on now as I ask myself how I feel after the first week of TC. Virtual Training Camp has pleasantly surprised me, and dispelled the worried I had before. The trainings have been amazing, the website challenge was definitely a challenge, but still a great experience, and the people are more amazing than I thought they could be. I have met so many amazing people in my class, and already forged some real connections. I am filled with an overwhelming sense of accomplishment, gratitude, and vindication.

I know the the last 2 years were absolutely worth it. I know that this is where I want to be. The cloud of existential dread that once loomed over me has dissipated. I am so grateful for everything in my life. I am amazed at the talent of my peers and feel lucky just to share a Zoom call with them. I am excited for the next 3 weeks of challenges and seeing the amazing work we produce. I feel a sense of purpose, community, and belief that I haven’t felt since that summer of 2016. For the last few years there were many moments when it felt like I was lost. Now, it feels like I am finally home and my heart is full.


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Posted in: Fellows, Inside VFA