From Pitch Stage to Real Growth: The Truth About Scaling Reach Pathways

Building While Flying: Lessons from Scaling Reach Pathways

When we won the Summerfest Tech Pitch in Milwaukee, it felt like validation.

Validation that our idea mattered.

Validation that the work Chicago Scholars had been doing for decades could translate into technology.

Validation that we could build something powerful for young people navigating college and career pathways.

But here’s the truth most people don’t see:

Winning a pitch competition is not the finish line. It’s the moment the real work begins.

Over the last couple of years, building Reach Pathways has required constant reinvention, hard decisions, and learning how to lead differently as the company evolves.

This is a reflection on what changed, what broke, what worked, and what I’ve learned along the way.

The First Pivot: From Building a Game to Building What Students Actually Needed

Our original concept centered around gamifying the college and career journey. We believed deeply in the power of engagement through gameplay.

And we were not wrong.

But we learned quickly that building a full game experience is expensive, slow, and difficult to iterate.

More importantly, when we went back and interviewed students, we heard something unexpected:

About half wanted a fully immersive game experience.

The other half simply wanted access to clear, structured information that helped them make real decisions about their futures.

That insight forced a critical decision.

Instead of building a complex game first, we shifted toward a simpler platform focused on access, guidance, and actionable learning. We kept the spirit of gamification through incentives, quests, and rewards, but grounded everything in practical outcomes.

The lesson:

Innovation is not about building what excites you most. It’s about building what your users actually need.

Designing Incentives Instead of Entertainment

Today, Reach Pathways uses “quests” and rewards to drive engagement. Students earn recognition for completing tasks that build real-world readiness:

• Exploring career pathways

• Practicing communication and leadership skills

• Learning AI literacy and ethical technology use

• Validating learning through mentors and peers

The goal was never entertainment for entertainment’s sake.

It was motivation with purpose.

Students didn’t want another learning management system that felt like homework. They wanted something that felt alive, supportive, and empowering.

Leadership Evolution: From Builder to Seller

One of the hardest transitions for any founder is recognizing when your role must change.

In the early days, my focus was validation and product development. We were proving the pedagogy, building technology, and testing whether our double-sided marketplace could work for both students and institutions.

Over the past year, my role shifted dramatically.

Less time building.

More time selling.

More time telling the story.

More time knocking on doors.

As founders, we sometimes romanticize product creation. But growth requires stepping into spaces that feel uncomfortable. Sales is storytelling with accountability. And if you believe in your work, you have to be willing to ask others to believe in it too.

The Power of Partnership (and the Myth of Doing It Alone)

One of the biggest accelerators for Reach has been collaboration.

We integrated other startups through APIs. We partnered with organizations aligned with our mission. We focused on ecosystem growth rather than isolated success.

Many founders operate from scarcity. The truth is that collaboration often creates more leverage than competition.

Some of our strongest growth moments came from simply being in the right rooms and staying active in the ecosystem.

You cannot scale quietly.

Building a Mission-Locked Company

Reach Pathways operates as an L3C, a low-profit limited liability corporation that bridges nonprofit mission and for-profit structure.

This model allowed us to align deeply with Chicago Scholars while still attracting investment and building a scalable platform.

It is not the easiest path.

But it has allowed us to pursue both outcomes:

• Sustainable business growth

• Measurable social impact

We raised nearly $2 million after Summerfest Tech and expanded to more than 40,000 users.

The biggest lesson here:

Find investors aligned with your mission. Not every dollar is the right dollar.

What Scaling Really Looks Like

People often assume growth is linear.

It isn’t.

For us, the last year has been about rebuilding the platform, launching a new version, and then seeing growth accelerate quickly once the foundation was right.

Today, Reach serves thousands of young people through partnerships with universities, social impact organizations, and workforce programs.

But scaling has meant constant adaptation:

• Adjusting product direction

• Hiring differently

• Sharing leadership

• Revisiting assumptions

Growth requires letting go of earlier versions of yourself.

Looking Ahead

The next phase of Reach is focused on expansion through partnerships.

We are working with:

• Organizations preparing young people for careers

• Institutions supporting workforce readiness

• Companies onboarding early talent

The vision is simple:

Help young people discover their futures and walk into opportunity prepared, confident, and ready to lead.

Final Reflection

If there’s one lesson I would share with other founders, it’s this:

You are always building while flying.

There is no moment where everything is figured out.

There is only clarity through movement.

And when your mission is strong enough, you keep moving forward even when the path shifts beneath you.

—

Jeffery Beckham Jr.

Co-CEO, Reach Pathways

CEO, Chicago Scholars