What Actually Works in Entrepreneurship Training (And What Doesn’t)
(Image: Fran/Kitchen of Purpose)
Most people don’t dream of building a billion-dollar company.
They dream of paying rent, covering daycare, and maybe—just maybe—doing something they enjoy on their own terms.
The truth is: the majority of aspiring entrepreneurs in underserved communities aren’t chasing venture capital.
They’re chasing stability.
What Doesn’t Always Work
Across the field, I’ve seen programs designed with great intentions—strong content, expert-led sessions, impressive toolkits. But when it comes to supporting first-time entrepreneurs, especially those balancing multiple jobs, caregiving responsibilities, or limited resources, these well-structured programs can sometimes miss the mark.
It’s rarely about doing things “wrong.” More often, it's a mismatch between what’s offered and what’s truly needed for the majority of folks at the starting line.
And if knowledge alone were the solution, YouTube would’ve closed the gap a long time ago.
From my experience, what many first-time entrepreneurs need is:
A structured path they can follow
Encouragement when things feel hard
Accountability
A real human cheering them on
And yes—some hand-holding, especially in the early days
What Does Work (Grounded in Practice)
Through years of co-designing and managing programs with nonprofits, local governments, educational institutions, and community partners, I’ve seen what helps participants not just learn, but build—step by step, with clarity and confidence.
Here’s what has consistently created traction for first-time founders:
1. Motivational Coaching + Mindset Work
Before the pitch deck comes belief.
Many entrepreneurs we support have never been told they can do this—let alone supported as they try.
Confidence-building isn’t fluff—it’s foundational. Programs that intentionally create space for mindset work often see stronger engagement and better long-term outcomes.
2. A Structured, Clear Path
The challenge usually isn’t a lack of information—it’s knowing where to start and what to do next.
That’s why we focus on developing simple roadmaps, checklists, and milestone goals that guide participants through the process.
“I’ve taken classes before, but this is the first time I actually started making progress. The steps helped me stop overthinking and just move.” —recent incubator participant
“I’ve never felt so clear about what to do next.” —recent incubator participant
That kind of clarity builds momentum.
3. Human-to-Human Support
Mentorship, peer learning, and real-time feedback go a long way.
Nothing replaces the trust that forms when participants feel seen, supported, and surrounded by people who genuinely want them to succeed.
We’ve found value in weekly live sessions, peer accountability partnerships (Purpose Partners), and guest speakers who reflect the lived experience of the communities we serve.
“The Purpose Partner idea really helped me stay focused. I actually looked forward to checking in each week.” —recent incubator participant
Real people, sharing real stories, spark real breakthroughs.
4. Tools That Match Their Lives
Technology can be powerful—but only when it meets people where they are.
Many of the entrepreneurs we support are juggling caregiving, shift work, or limited digital access. So we prioritize:
Google Docs over complex CRMs
Creative marketing strategies
Plain language handouts to encourage ongoing learning
Business models and plans written in plain language, not pitch decks made for investor panels
The goal is always accessibility without compromise.
The Bottom Line
If we want to see a stronger, more inclusive economy, we need to build entrepreneurship programs that meet first-time founders where they are.
To truly expand economic access, we need to consider more than just the curriculum. We need to ask: Is this clear? Is this supportive? Is this realistic for folks just starting out?
That means:
Starting with mindset
Offering structure
Centering relationships
Using tools that match real life
And above all—designing with empathy.
Let’s Build Better Together
If you're a nonprofit, city agency, or funder working to support first-time founders, I’d be glad to share more of what we’ve learned—and learn from what you’ve seen, too.
Feel free to reach out if you're thinking about launching or improving a program.
I’d love to be a part of the conversation.
This article also appears in my LinkedIn newsletter, Blueprints for Impact, where I share reflections, frameworks, and insights from the field. If you're building, operating, or funding programs that expand access to entrepreneurship, I'd love to connect.
