Traditional workforce programs train people to find jobs. But what happens when those jobs don't exist? SDA CEO Bo Kemp makes the case for entrepreneurship as workforce development, explaining how communities can create their own employers, expand business ownership and build stronger local economies.
Waiting for a major employer to relocate is not an economic development strategy.
In his latest Substack, Southland Development Authority (SDA) CEO Bo Kemp argues that workforce development needs to move beyond traditional job placement and embrace entrepreneurship.
Drawing on programs in Chicago's Southland and Gary, Indiana, Kemp explores how small investments, paid training and business ownership opportunities can help people create their own jobs.
He also examines the challenges facing traditional workforce programs, from artificial intelligence to retiring business owners, and explains how initiatives like SDA's First Founders can help build the next generation of local employers.
Stop Training People for Jobs That Aren't Coming
Waiting for an employer to relocate is a passive strategy. The regions that win will leverage Entrepreneurship as Workforce and proactively grow their own employers.
The Signal
In 2022, the Southland Development Authority ran a summer program for young people between 14 and 24 — the kind of young people most workforce programs quietly label "hard to employ."
For eight weeks, they worked, and they met with us. Not just to learn how to show up on time and fill out an application, but to learn how a business actually works: what a customer is, what it costs to deliver a service, how you price it, and how you get paid. At the end, they pitched us. Real ideas, from people most systems had already written off.
We were able to award a $3,000 grant to one of those teams to launch a local landscaping business.
Three thousand dollars. That's roughly what the public workforce system spends to train and place a single adult in a job.
I'd seen this movie before. In Gary, Indiana, we built a 12-week program for people who had just come home from prison. Half of each day was classroom work and life skills. The other half was paid work on crews with local landscaping companies. Twenty-five people started. Twenty finished. Fifteen of those twenty got full-time jobs. The other five launched their own businesses.
Every single person who completed that program was working — either for someone else or for themselves.
Three years later, one of the participants, Bernard, spoke at an event. He told the room that if he had known he could make more than $35,000 a year cutting lawns, he probably never would have gone to prison in the first place.
Sit with that for a second. Bernard didn't lack work ethic. He didn't lack hustle. He lacked a visible path from the skills he had to an income he could build on.
That's not a character problem. That's a design problem.
The Story Beneath the Signal
Here's what those two programs reveal, and it's bigger than landscaping.
Most of our workforce strategy is built on a single assumption: that the jobs already exist, and the job of the system is to match people to them. Train the worker, place the worker, count the placement.
That assumption works reasonably well when the jobs are actually there. It breaks down in places where too many economic development plans still amount to waiting for a large employer to relocate, and hoping it brings enough jobs with it.
Waiting isn't a strategy. It's a passive posture dressed up as patience.
And three forces are about to make the waiting even more expensive.
The Silver Tsunami. Baby boomers own roughly half of all privately held businesses with employees in this country — by Project Equity's estimate, about 2.9 million businesses employing more than 32 million people. As those owners retire, many of those businesses will be sold to out-of-town buyers, absorbed by larger companies, or simply closed. Every one of them is an employer we either replace or lose.
AI. The next wave of automation won't just change factory floors. It will reshape entry-level office, administrative, and service work — exactly the rungs many people use to climb into the labor market. Training people for roles that are being redesigned in real time is a losing race.
The reach gap. The public workforce system does a respectable job for the people it actually serves — about seven in ten adults who go through federal workforce programs are employed six months after they exit. But it reaches a remarkably small slice of the people who need work. The core intensive federal workforce programs enroll roughly half a million adults a year, in a country with more than ten million people who are unemployed or stuck in part-time work they don't want. By that math, roughly nine out of ten people who need a better job are not enrolled in any workforce program that could help them get one.
Put those together and the conclusion is uncomfortable: we're spending most of our workforce energy matching a shrinking number of people to a changing set of jobs, while the businesses that actually employ our neighbors are aging out, and most of the people who need help never walk through the door.
The Problem Beneath the Problem
None of this is a new idea. Workforce boards and economic development organizations have tried to use entrepreneurship as a workforce tool for decades. Federal law already allows it. A U.S. Department of Labor pilot in Chicago, Cleveland, Los Angeles, and Portland gave dislocated workers coaching and up to $1,000 in seed money — and 18 months later, 68 percent of participants were self-employed versus 56 percent of a comparison group. Washington State actually requires its local workforce boards to offer self-employment training at a rate that matches demand.
So why hasn't it stuck?
Because the problem sits on both sides of the table.
The system isn't built to say yes. Workforce programs are measured on job placements and wages. A new business is hard to count, so frontline staff are rarely rewarded for recommending it. Unemployment insurance in most states — including Illinois — puts your benefits at risk the moment you spend your days building a business instead of applying for jobs. Only five states run active Self-Employment Assistance programs that fix this. Pilots get launched, celebrated, and quietly sunset when the grant ends.
And the people we're trying to reach carry their own weight. Someone without a job needs income this month, and a business rarely pays in the first six months. Early income can push a family off health coverage or food assistance before the business can replace it. There's no friends-and-family round in most of our neighborhoods. A criminal record can block a license, a lease, or a loan. And after you've been rejected by the labor market — or locked out of it — believing you can build something of your own takes a kind of confidence most people were never taught.
That last one matters more than any policy memo admits. You can't raise your net worth until you raise your self-worth. Bernard had the skills. What he didn't have was proof that those skills were worth building on.
The Core Idea
Here's the distinction that changes the conversation:
Traditional workforce development helps people take a job. Entrepreneurship as workforce development helps people make one — and every person who makes a job is positioned to create the next one.
When a placement works, one person is employed. When a business works, the owner is employed, and the region gains a potential employer, a potential buyer of a retiring owner's business, and a local balance sheet that circulates money where it was earned.
That's why I believe entrepreneurship may be the single best workforce investment available right now — especially for the people the current system struggles to reach: young people, veterans, people returning to the labor force after caregiving or illness, people coming home from prison, and communities that have been historically locked out of ownership.
And the cost isn't the obstacle we pretend it is. Nationally, the public workforce system has spent somewhere between a few hundred and a couple thousand dollars per adult participant, and in some local areas the cost per participant runs past $10,000 — before you divide by the share who actually land a job. A $3,000 launch grant with coaching isn't a luxury next to those numbers. It's competitive.
This isn't an argument against job training. It's an argument against treating job training as the only door.
The Structure: Four Moves to Make Entrepreneurship a Workforce Strategy
When I look at what made the Southland youth program and the Gary program work — and what made so many other well-intentioned efforts fade — I see four moves regions need to make before entrepreneurship becomes more than a pilot.
1. Count It
Ask: Does a business launch count as a successful outcome?
If workforce boards are only scored on placements, entrepreneurship will always be the program nobody recommends. Regions need shared metrics — business launches, owner income, jobs created by participants — that reward the outcome, not just the referral.
2. Fund the Runway
Ask: How does someone eat while they build?
Calculated risk, not reckless risk. That means seed grants, paid training, or self-employment allowances that let people pursue a business without falling off a cliff. Illinois has no Self-Employment Assistance program today. That's a fixable policy choice.
3. Pair It With Paid Work
Ask: Is this an either/or, or a both/and?
The Gary model worked because nobody had to choose. Participants earned while they learned, and they learned inside the industry they might one day own a piece of. The federal pilot found the same thing — more people ended up holding a job while building a business. Entrepreneurship works best as a parallel track, not a leap of faith.
4. Build the Ownership Pipeline
Ask: Where does this lead in five years?
The goal isn't just more side hustles. It's more owners. A region that trains first-time founders today is building the bench of buyers who can acquire retiring owners' businesses tomorrow — keeping those jobs, and that wealth, local. From operator to owner isn't a slogan. It's a succession plan for an entire regional economy.
What This Looks Like in Practice
At the Southland Development Authority, this is exactly why we built First Founders.
First Founders is designed to do three things the traditional system struggles to do at the same time. First, it reaches people where they are — including the roughly nine in ten people who need better work but aren't enrolled in any workforce program — and helps them move past the fear, doubt, and lack of evidence that keep good ideas stuck in their heads. Second, it does that at an investment per participant that is competitive with, if not better than, the cost of a traditional workforce placement. Third, it doesn't end at launch. First Founders feeds into our Acquisition Accelerator, because the founders we train today are the owners and buyers of Southland businesses tomorrow.
Picture a 23-year-old who's been cutting grass for a neighbor's crew every summer since high school. The old playbook sends her to a job center, where she's matched to a warehouse shift 40 minutes away by two buses. The new playbook asks a different question: what would it take for her to own the crew? A pitch. A grant. A mentor. A few commercial contracts. And maybe, in ten years, the chance to buy the regional landscaping company whose owner is ready to retire.
That's not charity. That's regional economic development that starts with the people already here.
The Move
This week, look at one workforce or economic development program in your region — public, nonprofit, or corporate — and ask three questions.
Does it count a new business as a success? Does it give people a way to earn while they build? And does it connect anyone to the chance to own something, not just work somewhere?
If the answer to all three is no, you've found the missing door.
And if you're the person who's been thinking about starting something but hasn't moved — start smaller than you think. Price one service. Land one customer. Collect the evidence that your skills are worth building on. Doubt is usually just a lack of evidence.
Final Thought
Bernard's line has stayed with me for three years. Not because it's tragic, though it is. Because it's preventable.
Somewhere in every one of our communities is a young person, a veteran, a returning citizen, or a mid-career worker who already has the skills to build a living — and the will to build a business — but has never seen the path laid out in front of them. Our systems told them to wait for a job. Nobody told them they could make one.
The regions that win the next decade won't be the ones that land the biggest relocation. They'll be the ones that stop waiting, and start growing their own employers.
Follow Bo Kemp for More Insights
What does sustainable economic development really look like, and how can communities make decisions today that strengthen their economies for decades to come?
Southland Development Authority CEO Bo Kemp explores these questions in his Substack, sharing perspectives on commercial development, regional investment, entrepreneurship, public policy, and the economic future of Chicago's Southland.
Read more from Bo Kemp and subscribe to his Substack for his latest insights into the challenges and opportunities shaping communities across the Southland and beyond.
About the Southland Development Authority
The Southland Development Authority, a not-for-profit economic development organization, is committed to driving equitable and sustainable economic growth in the South Suburbs of Chicago. Through innovative programs, strategic partnerships and impactful direct investments, the SDA is building a vibrant, inclusive economy that drives wealth growth for individuals, businesses and municipalities. Combined with the benefits of the South Suburban Land Bank and the Monarch Fund, the SDA serves as a model for regional development.
