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Milwaukee startup helps justice-involved individuals get, retain jobs: The Pitch


Eli Rivera
Eli Rivera (pictured) and his colleague Ruben Gaona are working to not only connect justice-involved individuals with jobs, but support them there.
Kenny Yoo/MBJ

More than 15 years after he was first incarcerated, Eli Rivera started speaking to students about his past experiences through his wife’s job at the University of Wisconsin-Milwaukee’s Helen Bader School of Social Welfare. 

Those talks became therapeutic for him, Rivera said, and ultimately revealed that he had never fully understood how growing up in poverty led to the choices that landed him in prison.

“That kind of sparked the flame,” Rivera said of his speaking events. “So I kept speaking in these classroom settings and sharing these experiences.” 

He then attended an anti-recidivism event that popped up on his LinkedIn feed in 2019, where he and future colleague Ruben Gaona – who were assigned to separate breakout groups – both coincidentally came up with similar ideas for helping justice-impacted individuals find jobs. 

The pair ultimately collaborated to create The Way Out, a startup that connects justice-involved individuals with employers online and continues to support them with resources after being hired.

“Not only do we have to get folks employment – get them in front of employers – but really we need to make sure that prior to and after they're in there that we're constantly supporting them with a network of supportive service providers and utilizing technology as a vehicle to keep everybody connected,” Rivera said. 

Founded in 2020, the startup’s mobile app works to reduce Wisconsin’s high recidivism rates by helping justice-involved individuals build a free profile to connect with employers. That profile is designed to contextualize potential employees by tracking their training, certifications and personal strengths.

The platform helps to prevent against conscious or unconscious discrimination from human resources departments for reasons like the person’s name, ZIP code or gaps in employment, Rivera said. 

While the company started its service in early 2021 by primarily connecting individuals with employers, it began to develop its revenue model around June of that year and now tracks employee retention, which is about 93% among its users, Rivera said. 

That high retention rate can be attributed to the support The Way Out connects users with for as long as they need it, which includes tech assistance, housing, health care and transportation, Rivera said. 

Since its founding, The Way Out has participated in Wisconsin startup accelerator gener8tor’s free four-week gAlpha program and in 2020 won $15,000 at the P5 Project & Milky Way Tech Hub Pitch Competition during Startup Wisconsin Week. 

Most recently, the startup won $100,000 and other Google benefits through the inaugural Google for Startups Latino Founders Fund

The company now sees a future in being able to partner directly with large companies to create employee pipelines, which could happen by working with a venture capital firm to scale their product, Rivera said. 

Large companies often have more stringent HR policies that initially made it hard for The Way Out to work with them, Rivera said. It will thus focus on receiving direct input from those companies – partially through help from their early funder American Family Insurance – as it grows while remaining a user-centric platform. 

“We want to make sure that we're getting the input of those that we're hoping to have a stake in the utilization of the platform,” Rivera said. “(We’re) getting a lot of feedback from the workforce development boards, working with HR and some of their technologies to just make sure that there's a higher level of compatibility and compliance.” 


Company name: The Way Out 

Headquarters: Milwaukee 

Year founded: 2020 

CEO: Eli Rivera (co-founder)

No. of employees:

Website: www.twout.org 


The product: A second-chance employment platform that aligns employers with qualified justice-impacted job seekers. It also connects the job seekers with additional re-entry and supportive service providers. 

How it makes money: Employers that are finding it challenging to hire and retain workers pay various direct hire fees, depending on the amount of employees they’re seeking annually. Those fees are calculated based on the employee's annualized salary.

Size of the market: $273 billion in potential direct hire fees, given that the U.S. labor market is short 10 million workers and there are over 70 million justice-impacted people in the U.S., according to The Way Out. 

Competition: HonestJobs and 70MillionJobs, who primarily focus on matching justice-impacted employees with second-chance employers, according to The Way Out. 

Competitive advantage: In addition to connecting employees with employers, The Way Out focuses on development and retention by offering ongoing training and support opportunities via its mobile app, Rivera said. 

Key leaders: Co-founder and CEO Eli Rivera, co-founder Ruben Gaona, partner and product manager Ryan Graham 

Capital raised: $350,000 through gifts, grants, non-dilutive funding, loans and income 

Capital sought: $2 million 

Ideal exit: 5-7 years for a total sale of $50 million+ 


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