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Aaron Kennedy on Navigating Setbacks in the Startup World | Foster MS in Entrepreneurship Alum Spotlight

Foster’s entrepreneurship program helped Aaron Kennedy persevere through challenges while building his startup, Outway.

The Outway team, led by Aaron Kennedy (bottom left), combines its talents to make land management more connected and effective.

Startups are built on constant decision points, strategic investments, and, as it turns out, the frozen food section at Trader Joe’s. Aaron Kennedy (MS 2021) knows all about the trials and tribulations of starting a business as the CEO, CTO, and Founder of Outway.

As the solo founder behind Outway’s successful launch, Aaron heavily leaned on the practical tools, frameworks, and networks he gained during his Master of Science in Entrepreneurship at the Foster School of Business. It was these same resources that helped him and his team persevere during their most challenging times, pushing them to bootstrap until they emerged on the other side.

Outway is a platform purpose-built for land managers, combining mapping, tracking, recording, and reporting all in one place. It’s a tool that offers a streamlined workspace where teams can work together, focusing on preserving and enhancing the land. At the same time, Outway takes care of the logistics in a visible, shareable, and impactful way.

In this Q&A, Aaron walks through the financial hacks, program lessons, and leadership decisions that helped him steer through challenges and keep his venture moving forward.

Outway is an all-in-one land management software as the backbone for how government operations manage nature at scale, from wildfire mitigation to recreation to wildlife protection.

Tell us about a time you were at a professional crossroad and what influenced the path you took.

Aaron Kennedy: I was six days out of a gruelling shoulder surgery when our company ran out of runway for the second time. That was a brutal, gut-punch moment.

We had raised friends-and-family money, built the minimal viable product, and even convinced some hard-to-win-over government clients to ditch their old tools and adopt ours. Just as we were about to close four venture capital term sheets, Silicon Valley Bank crashed, and every one of them pulled out. Breaking that news to the team had me teary-eyed, but they all looked back at me and said, “We’re not done yet.”

That conviction, paired with customer traction, made me choose bootstrapping over folding, and we kept the lights on with contract work until Wildwood Ventures came in as a marquee partner.

Whether biking, skiing, or whitewater rafting, Aaron Kennedy (MS 2021) finds energy and perspective outdoors, the same spaces his venture, Outway, is designed to help preserve.

How did you make founding a startup work from a personal finance perspective? Any tips?

Aaron Kennedy: Trader Joe’s (that’s only half a joke). I tracked my meals down to an average of $4.23 each while still eating healthy. We ran the company in “hybrid entrepreneurship” mode, funding Outway by taking on consulting work in DTC business ops systems.

That gave us a full-time income for a half-time commitment, freeing the rest of our hours for our startup. Pairing my Trader Joe’s food budget with aggressive savings on rent, groceries, and tools kept us afloat for six months. Even our tech stack reflected this mindset: serverless architecture trimmed our Amazon Web Services bill to under $300 per month, essentially paying only for our database and live usage.

What aspect of the MS in Entrepreneurship continues to pay off?

Aaron Kennedy: Many classes in the MS Entrepreneurship made an impact, but there are a couple of standout lessons that I still lean on today:

Autonomy, pursuit of mastery, and purpose motivate people more than just money and equity.

Navigating a start-up is like getting to a lighthouse through a foggy forest. The lighthouse is your vision, but you can only see the next 10 steps in front of you. Use the lighthouse as your north star, but react and respond to changes in front of you as they arise.

Startups fail far less than their founders give up. Know when to give up and when to persevere, and to do that, you need to surround yourself with mentors who will challenge you in both directions.

Marketing is not optional. Even if you build it, they won’t come unless they know it exists. Every single person you talk to could be a customer, an advocate, a fan, or an investor. So, build your network and audience constantly and relentlessly from day one.

Outway’s platform in action: bringing mapping, tracking, and reporting tools together in one streamlined workspace for land managers.

If you were to start your entrepreneurial journey over again, what would you do differently?

Aaron Kennedy: That’s easy.

1. Charge immediately. We learned the hard way that true validation comes from transactions, not compliments.
2. Treat networking like oxygen. Add everyone you meet on LinkedIn, start content early, and automate outreach. You’ll have 1,000+ connections by the time you graduate. Include all your social media links, your website, and your LinkedIn profile in the footers of every email.
3. Set hard rules for when to persevere, pivot, or quit. There’s always just enough validation to argue either side, but accountability to pace is paramount.
4. Go deep on “compounding engineering” with AI from the first day. Invest in systems that continuously improve themselves. It multiplies the capacity of small teams far more than even brute-forcing GPT on individual tasks.

Aaron’s story shows how resilience, resourcefulness, and the right support system can turn setbacks into stepping stones. His journey through the MS in Entrepreneurship program highlights how the Foster School of Business (and Trader Joe’s) equip founders to navigate uncertainty and keep their ventures moving forward.

Learn more about the Master of Science in Entrepreneurship program here.