Where the Road Meets the Jungle: Advice on Pursuing Entrepreneurship While Securing Your Future | MBA Career Peers Series

By Ty Dewes, MBA ’24 | MBA Career Peers

Leaving the well-trodden path of Big Tech, I embarked on my MBA journey at MIT Sloan eager to explore and create impact in my area of interest, Education. I was exhilarated by the thought of joining an early venture or even launching my own startup because it represented a direct avenue to effect meaningful change. MIT Sloan offered a safe space to explore my entrepreneurial ambitions backed by a tried-and-true academic and professional support system.

However, the pragmatic side of me couldn’t ignore the financial realities and uncertainties that come with the entrepreneurship territory, especially with my limited experience at startups prior to MIT Sloan. Questions began to pop up: “Would I thrive in the intense startup culture?”, “Could I find a founding team I loved working with?”, and “Could we realistically find success?” What became clear to me was that I needed balance — a strategy to explore entrepreneurship while building an attractive safety net for the unpredictable.

Now, I can’t in good conscience recommend everyone embark on this forked path. Taking the challenge of juggling startup aspirations with the academic rigor of MIT Sloan and coupling that with industry exploration and recruitment demands a lot. It is a careful dance of prioritization, decision-making, and, most importantly, self-reflection, but I want to share my story along with the tools and resources available at MIT Sloan to support you in this endeavor.

Please know that your mileage may vary with these tactics and everyone’s journey at MIT Sloan is unique. Instead of taking these items as a checklist, instead, think about which tools may be useful to you in your exploration.

Setting the Course: Define Goals and Boundaries

The first step in this dual exploration was to outline what I truly wanted from my MBA and entrepreneurial pursuits. Sitting down with peers as well as the Career Development Office (CDO) was my way to brainstorm and probe at my deeper non-negotiables which ultimately came down to:

  1. Facilitating technological innovation in the K-12 education space;
  2. Pursuing a product-centered role at a tech-forward company; and
  3. Finding a location and team conducive to my personality and working style.

These ‘north stars’ became my guides as I began to explore the breadth of opportunities at MIT Sloan — both entrepreneurial and otherwise — helping me to both understand and stay aligned with my long-term objectives, especially amidst the recruitment FOMO as my peers began to travel down more trodden paths.

Forging a Path: Start Early and Be Loud About Your Passions

Two years seems like a long time, but it goes by faster than you’d think. And so, it’s crucial from the outset to make a conscious effort to create and embrace new opportunities while at MIT Sloan. Fortunately, MIT Sloan provides ample opportunities in your first year to test the entrepreneurial waters. By getting involved in (1) MIT Sloan’s rich networking (social) opportunities, (2) courses like the E&I Pro-Seminar, and (3) joining any of the numerous industry or role-related clubs (quick shout-out to the Education and Entrepreneurship Clubs), you can efficiently find a network of similarly passionate students that are looking to change the world for the better. Then, the key is to leverage this network to seek out and create opportunities.

The most effective method I’ve found to do this is to be vocal about your passions. This looks different for everyone, but whether it’s speaking up in a class about your passion for sustainability or inviting someone from the Education Club (no, really, join our club) to coffee, the more people who know your interests and passions, the more you’ll see the truth in the phrase, “Sloanies helping Sloanies.” People can only help you when they know what you’re looking for.

Personally, I made it a point to tell everyone I met about my obsession with EdTech. This ultimately led me to my co-founder through a friend who introduced us at a Red Sox game after remembering that I didn’t stop talking about education that one time over coffee. Remember, opportunity is not there for the taking; it’s there for the bold to forge and the passionate to seize.

Finding your Comfort Level: De-Risking is the Name of the Game

In entrepreneurship, risk is a constant companion. My approach to bearing it was to strategically de-risk our venture, balancing my entrepreneurial ambition with caution.

One way I did this was by enrolling in entrepreneurship lab classes like Venture Creation Tactics. Here, I wasn’t just learning about entrepreneurship in theory, but also garnering dedicated time as well as practical resources and insights to build my venture alongside some of the foremost minds in entrepreneurship research. Our team was also able to tap into resources like MIT Sandbox and the AI Pillar collective to find both mentorship and financial support. Seeking out and engaging with seasoned entrepreneurs and innovators across campus created guardrails for us to navigate our early startup growth while providing us with practical tools, strategies, and confidence as we scaled our venture.

At the same time, I was also concerned about my career pivot beyond the startup and was keen on exploring non-startup roles that aligned with my north stars to serve as a pragmatic safety net. This exploration was more than a backup plan, though. It was an intentional pursuit aimed at introducing myself to product management industry practices and broadening my professional skill set both for my own exploration and as an asset to our venture. This ultimately manifested in balancing both a product management internship while also pursuing my startup over the summer.

While I’ll discuss more of what this looked like in practice below, this is the valuable lesson here: you are the master of your own risk and comfort levels in your startup journey. Whether bearing that risk means pursuing entrepreneurship full-time or balancing it with other ongoing priorities, it’s crucial to take a step back, assess your thresholds, and decide what’s right for you amidst your values. After all, everyone’s journey is unique, and what works for one person may not work for another.

Striking the Balance: Maintain Transparency and Focus

Now the big question at this point is usually, “How did you balance the startup with an internship over the summer?” I cannot stress enough that this is by no means an easy endeavor, but two important pieces of the equation were rigorous transparency and focus.

In her book Radical Candor, Kim Scott advocates for organizations to adopt a radically candid communication style that prioritizes transparency, i.e., free-flowing information. While I knew it would be a difficult conversation to have, I sat down with my co-founder/founding team and internship manager/team (separately) and laid out clear goals and expectations for both commitments. I explained my rationale for this dual exploration, emphasizing how each experience would enrich the other and how that aligned with my own personal and professional aspirations. This approach not only helped in setting realistic expectations for my teams but also fostered an environment of mutual respect. By being upfront about my commitments and limitations, I was able to better navigate and rationalize conflicts and ensure that my contributions were focused and impactful in both roles.

A word of caution. Not only is transparency an ethical consideration here, but it may also be a legal one. Making sure your employer and your team are in alignment with how you prioritize and manage both opportunities is necessary. This involves adhering to any contractual obligations or non-compete clauses that may exist with your employer. This proactive approach not only protects you legally but also upholds a standard of integrity and professionalism across your commitments.

In addition to transparency, my focus and time management was critical.  I had to strategically allocate time, often planning well in advance, to meet the demands of both my internship and startup. This involved sacrificing personal time in both the mornings and the nights to focus on whatever was most pressing. Setting specific, achievable goals for each role and sharing these goals with stakeholders at both companies kept me focused and accountable, ensuring that my work was always properly prioritized, concentrated, and effective.

More importantly, self-care was a necessity. Balancing intense roles can be draining, so making time for both mental, physical, and social rejuvenation was crucial for maintaining my overall productivity and well-being.

While there were certainly times I felt exhausted over the summer, I never felt defeated. Juggling an internship and a startup was an incredibly valuable and rewarding experience to develop a diverse skillset while providing a comfortable (for me) level of exploration and safety. My TLDR for anyone embarking on a similar path is: Maintain open communication, be strategically mindful of your time, and never lose sight of your north stars as well as your personal well-being. It’s about finding your rhythm in the chaos, understanding your limits, and pushing them responsibly. MIT Sloan offers an incredibly unique playground to test your boundaries and grow, and it is up to you to do so wisely.

Remember, there’s no one-size-fits-all approach to managing your exploration at MIT Sloan. What worked for me might not work for you, and that’s okay. The beauty of this program lies in its uniqueness to each individual. So, as you navigate through your own MIT Sloan adventure, embrace the uncertainties, learn from every experience, and above all, stay true to yourself.

If you’d ever like to connect, I can be reached at tydewes@mit.edu.


At MIT Sloan, we reference the different recruiting paths to MBA-level opportunities. What do we mean by Highway / Dirt Road / Jungle?

  • Highway: MBA-level jobs with a structured recruiting process, often conducted through campus. This includes, but is not limited to, Consulting, Investment Banking, and Leadership Development Programs.
  • Dirt Road: Opportunities within industries whose recruiting processes for MBAs are less defined, requiring more networking and individual outreach. This includes opportunities in Private Equity, Venture Capital, Media/Entertainment, and Sports.
  • Jungle: Starting a new venture, pursuing positions with start-ups and early-stage ventures, or unstructured MBA opportunities.
By MIT Sloan CDO