Blog | Loeb.NYC
Blog | Loeb.NYC

Internatopia: An Internship Experience Like No Other

Charlotte Medway and Courtney Halle

To launch our annual paid summer internship program, two interns, Charlotte Medway and Courtney Halle, give us their perspective on the program so far.

Playing the Long Game

Summer internships are considered an important and recommended part of the undergraduate college experience. They provide students the opportunity to develop their career aspirations, learn professional skills and grow their network. With loose experiences in the entrepreneurial space, we both understood the agile, fast-paced and iterative nature of startups and were looking forward to the opportunity to make a genuine contribution to a growing business. 

The internship experience goes above and beyond expectations. From the moment we stepped off the bus to begin training at Michael Loeb’s Hamptons home, it became clear that is dedicated to its people. Internatopia is a testament to the integrity of the company’s mission. As “people-first investors”, the retreat’s focus on entrepreneurial education demonstrated the company’s commitment to developing human capital. is playing the long game, taking time to organically develop the capabilities of its portfolio companies and interns alike.

CEO and founder, Michael Loeb generously opened the doors to his Hamptons home, inviting forty incoming summer interns to join his chef’s table – both figuratively and literally (rest assured, the phenomenal meals did not leave any intern hungry). Appropriately titled, Internatopia was a retreat designed to immerse interns in the world of entrepreneurship, opening conversations about creative thinking, disruptive innovation, persistence, and grit. 

internatopia interns poker

Playing with Risk 

Instead of the common – and often uncomfortable – icebreakers played in our previous summer internship orientations, Rae Cloud, our internship program coordinator, had something else in mind. She surprised us with an untraditional way of getting to know one another: lessons from professional pool and poker players. 

Using their unique skill sets, these individuals taught us strategies to apply to our everyday tasks in order to be successful in the startup space. 

At the poker table, several key lessons were reiterated. We had both played poker in the past, so the game’s instructions were not particularly surprising. What was surprising, however, was how these themes applied to the bigger picture: succeeding at and beyond.

Making a calculated risk in poker is essential – your money is on the line and it is necessary to read your competitor, and their strategy, as accurately as possible. It is important to know when to call and when to check by using the resources around you. It is also crucial to remain patient and wait to be dealt the right hand. This is all happening simultaneously and it requires awareness of both your own actions and those of others. This includes thinking ahead to possible scenarios and how to react to game-time decisions without “blowing your cover.”

These lessons correlate to being a part of a startup as well. Statistically, only 1 in 10 startups actually succeed. This presents a high risk for the few entrepreneurs who are brave enough to pursue their idea. Success requires thinking ahead of your competitors and doing your best to anticipate the next big move, despite occasionally being blindsided by the unknown. Success means keeping your cool and being diligent by always having your end goal in mind. 

From the Poker Table to the Business World

  1. Use the resources around you to make the most strategic and calculated decisions
  2. Don’t be too proud – observe your environment and be willing to change tactics 
  3. Be patient. Success takes time 
  4. Always think ahead
  5. Keep your cool if things go wrong 

For us interns, the stakes were low. We were playing with fake money that had no risk attached. Our competitors were our peers who became fast friends by the end of Internatopia. Overall, we learned invaluable skills that we can all apply to our summer at 

Getting Equipped

Day two of Internatopia resembled an entrepreneurship ‘Think Tank. We were lucky to hear from leading entrepreneurs who directed the conversation toward the key pillars of innovation. 

We heard from Connor Blakley, a young entrepreneur who founded Youth Logic at age 17. Connor spoke to the value of realizing gaps in the market and challenging the status quo in order to grow a business. Connor also motivated the audience of interns to challenge age barriers, a lesson reiterated by a later speaker, twenty-four-year-old Noah Friedman. 

Noah initially joined as an intern and transitioned into COO of one of’s portfolio companies, 3×3 Insights. Using a rocket ship analogy, Noah demonstrated the opportunity for interns to grow and develop their careers. 

noah friedman

“If you snuck your way onto a rocket ship and started driving it, nobody would question your age or your credentials. All that matters is that you proved you were able to drive it.”  – Noah Friedman

Later in the afternoon, the interns heard from Michael Loeb himself. He began by paraphrasing Thomas Edison on the creation of the lightbulb:  “I have not failed. I’ve found 10,000 ways that won’t work.” Michael introduced his concept of the entrepreneur’s gene, outlining the character traits that make for a successful entrepreneur. He emphasized the importance of adaptivity and challenging traditional operations, highlighting the risk of complacency which can result in inefficiencies. 

For such an accomplished and successful individual, it was surprising how easily Michael connected with our cohort of incoming interns. It stood as a testament to his approachability as a humble leader and demonstrated his genuine interest in our growth and development. 

michael loeb southampton internatopia

The Entrepreneurs’ Toolkit

  1. Think outside the box and challenge the status quo
  2. Age is just a number 
  3. If it does not work, try again! 

Internatopia included a fun ‘Pitch-off’ between the three most popularly voted intern business ideas. Charlotte Medway pitched her idea for a live social platform connecting users and venues – an app people can use when they want to go out. Felipe Corredor presented his idea for a wearable wrist technology geared towards mindfulness. Finally, Rudra Ramchandran presented his idea for a reusable water pasteurization indicator vessel which tackles the growing problem of drinkable water scarcity, particularly in remote areas. 

The ‘Pitch-Off’ was a chance for interns to enter an open dialogue with the ‘shark investor’ panel of professionals, including Michael Loeb. The panel shared their expertise, questioned ideas and suggested future actions. Michael was willing to connect interns with his impressive network of contacts to give them a step up in pursuing their ideas. 

demo day internship summer


Day Three was busy and exciting. Rich Vogel, Loeb’s CFO and COO, addressed the interns and company representatives about his journey to success. 

His story was centered around the theme of grit. Vogel mentioned the book Grit: The Power of Passion and Perseverance by Angela Duckworth. This type of attitude – being a go-getter – is quintessential in the startup space, as grit differentiates the most successful entrepreneurs from others. 

rich vogel career growth

“Fall seven, rise eight”  – Rich Vogel quoting a Japanese Proverb

Rich recalled his journey from childhood to his professional life. Throughout his recollection, he emphasized the importance of a strong work ethic. He believes working hard is equally important as being naturally talented. 

As interns at a highly successful venture collective, this was inspiring to hear because of its attainability – we are all beginning a challenging yet rewarding ten-week journey. We have been granted access to incredible resources and opportunities through’s investment in all of us. By possessing unwavering grit, we can achieve success. 

Beginning Our Journey 

Overall, Internatopia far exceeded our expectations for ‘summer internship training’. Instead of being fed instructions and given tedious introductory tasks, we were able to learn by actively participating in discussions and having real conversations with company representatives. By establishing an environment that emphasizes the importance of communication and connection before the onset of our internship, gave us the confidence we need to succeed for the next ten weeks and beyond. 

paid summer internship loebnyc

Sign up for our Quarterly Digest

Receive the latest news, insights, and inspiration from's venture collective.