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Building an Inclusive Workforce with Second-Chance Hiring

Building an Inclusive Workforce with Second-Chance Hiring

Working Fields Offers a Path to Employment and Confidence to Formerly Incarcerated People and Those in Recovery 


Mickey Wiles is the CEO and Founder of Working Fields, a mission-driven staffing agency that helps individuals overcome barriers to employment — such as substance use disorder, criminal justice system involvement, resource challenges, or work history gaps — and build stable futures. A U.S. Navy veteran, Mickey has worked in leadership roles at Ben & Jerry’s, Seventh Generation, and Burlington Labs, and served as Executive Director of Turning Point Center of Chittenden County, Vermont. Mickey is a person in long-term recovery and was provided a second chance after spending time in federal prison. 

For the last 18 years, Mickey has dedicated himself to helping others who need a second chance after addiction and/or criminal convictions. By collaborating with businesses across Vermont and New Hampshire, Working Fields has fostered a community of recovery-friendly workplaces that treat people in recovery or those with past convictions as they would treat anyone else.

In this conversation, The Kassan Group founder Jenny Kassan chats with Mickey about how Working Fields is contributing to the development of an inclusive, regenerative economy.


Jenny Kassan: How do you stay true to your business’ foundational principles while also being flexible enough to meet the shifting challenges of the day?


Mickey Wiles: Our foundational principles are reflected in our company values: love, humility, honesty, equity in action, stability, and gratitude. Our team keeps these values front and center by focusing every two months on the continued development of a different value. Our leadership team, which meets weekly and addresses the issues and challenges of a changing environment, always considers the company’s values in making company decisions. We embrace change, flexibility, and agility as long as we also always challenge ourselves to make decisions consistent with our values.


JK: Your company helps foster healthy and resilient communities. As we face large-scale challenges on a global scale, to what extent do you consider social entrepreneurship “borderless” and to what extent do solutions need to be localized? 


MW: Social entrepreneurship means placing people, planet, and prosperity for all at the core of business. These principles apply across the board regardless of where we operate. If we collectively operate with other like-minded businesses, then our reach is borderless. However, with this as the premise, our challenges are to be inclusive and take into consideration all individuals, recognizing that different societal groups have different needs and practices. As we expand and serve communities and varied groups of people, we need to always be aware of these differences.


JK: How do you see the practices and core values of your business as distinct from the “business as usual” status quo? What do you do to resist the pressure to “fit in” to the old economy paradigms?


MW: Avoiding “business as usual” is not a difficult task for us as our mission and vision are so different from other organizations in our space. When we remain true to our mission, we automatically are not operating as “business as usual.” We have faced situations that raise questions in light of our company values. In that case, we invite everyone in the organization to discuss the opportunity and the pros and cons. We gain input from everyone to ensure we hear all arguments. Then we make a decision based on that input and the leadership team’s assessment.


JK: Who inspires you in the social impact world and what is the one question you’d like to ask them?


MW: I’ve been fortunate to work with and learn from three fantastic leaders in the social impact world. I first worked for Ben & Jerry’s when social impact businesses were not as common as they are today. Both Ben [Cohen] and Jerry [Greenfield] led us to not accept the status quo and to challenge every decision we made to ensure it took into account our “triple bottom line” (that’s how we referred to social impact business). My next mentor was Jeffrey Hollender at Seventh Generation. His leadership demonstrated that there was an additional level of impact businesses can have on the world. I would ask all of them the same question: If you had to do it over again, what would you change and how would you counsel your younger self?



Mickey Wiles is the CEO and Founder of Working Fields, a mission-driven staffing agency that helps individuals overcome barriers to employment — such as substance use disorder, justice involvement, resource challenges, or work history gaps — and build stable futures. 

Mickey has had a long career in the private sector business community where he held various leaderships roles starting with a Boston high tech firm, Microcom, Inc. In Vermont he continued in leadership roles with Ben & Jerry’s, Seventh Generation and Burlington Labs. Mickey also held the position of Executive Director at the Turning Point Center of Chittenden County. Prior to starting his business career, Mickey served six years in the United States Navy.

Mickey is a person in long term recovery and was provided a second chance after spending time in Federal Prison. For the last 18 years, Mickey has dedicated his work to helping others who want a second chance after addiction and/or criminal convictions. Mickey is on the Board and Executive Committee of VBSR, the nation’s first business association of businesses for social responsibility. Mickey is also President of Vermont Roots & Wings Alliance, an organization dedicated to supporting the drug court system and participants in Vermont. 



Working Fields is a mission-driven staffing agency that helps individuals overcome barriers to employment — such as substance use disorder, justice involvement, resource challenges, or work history gaps — and build stable futures. 

We don’t just place people in jobs: Our model includes robust, personalized support for workers. Every Working Fields associate benefits from direct account management, ongoing peer recovery or life coaching, and coordinated support from community partners. These services enable our associates to get and keep the jobs they want, while helping employers realize the potential of these dedicated workers. 

We work closely with community partners, particularly social service agencies, across Vermont and in Manchester, New Hampshire, to identify individuals in need of supportive employment services. These referrals have enabled us to help over 1,300 jobseekers since 2017.  



Building a Strategy to Fund Your Business On Your Terms

In this video, The Kassan Group founder Jenny Kassan outlines six important steps to designing your fundraising strategy.

Funding is an essential element of starting a business, but figuring out the best way to acquire it can be challenging, especially for mission-driven entrepreneurs who don’t want to give up their values to get their business off the ground.

In this video, Kassan Group founder, Jenny Kassan discusses her six-step process for raising capital without selling your soul. According to Jenny and her team, “The way you raise money should be consistent with what’s important to you and your business.”

These six pillars will lay down the proper foundation for your business to succeed while keeping your mission intact. This process consists of defining your goals and values; identifying your ideal investors; designing your offer; choosing your legal compliance strategy; creating an effective investor enrollment strategy; and addressing potential obstacles. Learn more about building the six pillars of your fundraising strategy in the following video.

The Kassan Group is planning a three-day virtual training to take a deep dive into these steps. If you’re looking for guidance on building a fundraising plan for your business in a way that meets your values, join us! Register for the event November 2-4 at


How to Find the Right Investors for Your Small Business

In this video, Jenny Kassan describes a way to raise money for your business that lets you stay true to your goals and values and keeps you in control.

Every business needs funding to get off the ground, but determining the best way to attain it is no easy feat. Small business owners may think they have only three options: find investors via the venture capital (VC) path, take out a loan, or go the bootstrapping route. None of these options work well for the majority of businesses.

Fortunately, there is another way. In this video, Jenny Kassan, founder of The Kassan Group, shares how to raise money for your business without compromising what’s important to you. “You can get your business funded without having to sell your soul or give up control of your business.” 

Jenny recommends designing an investment opportunity that fits your business and to broaden your idea of who your investors could be. It’s important for business owners to remain transparent when discussing terms with prospective investors and to balance the investor’s needs with their own. This will help you find the right investors who come in on terms that are consistent with what you want for your business. Learn more about customizing your investment offering and getting creative about who your investors are in this video.



Looking for the right investors to help you grow your business? Sign up for our free email series and discover the 6 steps to finding values-aligned funding sources to help you achieve your goals! With the steps outlined in this series, you can make the process more efficient, less intimidating, and—dare we say it?—FUN! Sign up here.

Three Insights from My Trip to Baltimore to Meet Potential Investors

Three Insights from My Trip to Baltimore to Meet Potential Investors

I recently returned from a trip to Baltimore where Michelle Thimesch and I met with several potential investors for Opportunity Main Street, our place-based investment fund.

I love the process of raising money for my own business because I always learn so much that I can use to benefit my clients! I started helping entrepreneurs raise capital over 16 years ago and this is my fifth time raising money from investors. I have raised over $2 million from a total of over 150 investors, with check sizes ranging from $1,000 to $100,000.

Here are three insights I wanted to share from my previous and current fundraising efforts:

1. Investors can come out of nowhere. Sometimes the people that end up investing are not who you expected! We met with someone in Baltimore and didn’t even “pitch her” but she ended up letting us know she wanted to invest. The lesson from this: tell everyone (without violating the law!) that you are raising money – don’t limit your asks to the usual suspects.

2. The timing is not in your control. We have had several potential investors tell us they planned to invest and we celebrated, only to be reminded that a verbal commitment doesn’t always mean an immediate check in the mail. Unexpected events like illness, bureaucracy, financial setbacks, and many more can slow the process way down. The lesson from this: be patient and persistent.

3. Investors’ motivations are complex and incredibly diverse. Some of our investors are interested solely in our mission and asset class and are happy to be passive, while others are motivated by a desire to get involved by supporting the entrepreneurs we work with. The lesson from this: brainstorm a list of all the potential benefits an investor can receive from investing in your venture – financial, educational, connections, community . . . – and know that each one of these benefits may be what motivates someone to say yes.

For details on our current fundraising efforts, please visit

Closing the gaps in the regenerative investment ecosystem

Closing the gaps in the regenerative investment ecosystem

My colleagues and I are on a mission to create a robust infrastructure and ecosystem that will make regenerative community investing easy, seamless, accessible to all, and fun!

To this end, we have put many pieces in place: legal/coaching services (Jenny Kassan Consulting), a community investment platform (Crowdfund Mainstreet), and an investor community open to all (Angels of Main Street). We are always asking ourselves what else we can do to support the movement for community investing.

One big missing piece is welcoming and inclusive physical locations where entrepreneurs, investors, and allies can come together to connect and build trust. In the last year and a half, we have all come to appreciate in-person gatherings. The human species was not designed to connect via video camera! Yet coming together in person continues to be challenging, especially for small businesses whose livelihoods depend on being able to meet customers face to face.

Michelle Thimesch and I have launched an investment fund called Opportunity Main Street with the mission to lift up and sustain overlooked entrepreneurs and the investors who want to support them by providing a physical location where they can meet and share resources. We are thrilled to announce our first investment—Charm City Inn, a beautiful building in Baltimore, MD.

The building will be a hub for community investing—a place where entrepreneurs can connect with local investors, sell their products in a cooperative retail space, and produce products in a commercial kitchen. It also includes short term residential units and a pub/eatery in the basement.

By providing affordable cooperative space for entrepreneurs with shared resources like a point-of-sale system, shared staffing, and meeting space, we can help them ease back into community-facing businesses without having to bear all the risk and expense.

Opportunity Main Street is offering the opportunity to invest in this project through secured promissory notes at 7% interest and preferred equity with a projected 12-15% IRR. This offering is only open to accredited investors. The last day to invest is September 28.

Please email for details!

Three Keys to Escape the Bootstrap Trap

Three Keys to Escape the Bootstrap Trap

You may have been bootstrapping for a while now—using your personal resources to fund your business and hoping that eventually you will be able to break even and start paying yourself and buying the things your business really needs. 

The symptoms of being in the bootstrap trap include:

  • using personal credit cards to pay for business expenses
  • doing side gigs to earn extra money
  • wearing all the hats in your business because you can’t afford to get high-quality help
  • not being able to provide a top-quality customer experience due to lack of funding
  • not paying yourself a salary anywhere close to what a CEO should earn

Going for too long with too few resources is a leading cause of business failure. So how do you finally get off the hamster wheel of bootstrapping?  Here are the keys to get on the right path:

Realistically evaluate your options and commit to the best one for you.  

If you are in the bootstrap trap, you have three options:

1) Continue as you are and keep hoping that you finally get enough revenues to be able to do all the things you want with your business. This can work for some—if you hustle hard enough you may be able to reach that revenue goal. But if you have been trying to reach that goal for a while and you keep falling behind, it is time to acknowledge that a lack of resources is making it impossible for you to create sustainable revenue. You are in a vicious cycle!  Without upfront resources, you can’t buy what you need to create a business that generates sustainable revenue.

2) Give up on your business and get a job.

3) Bring outside resources into your business—also known as Other People’s Money (OPM). I want to be very clear about what OPM is. It is not money that you are personally liable to pay back (like a credit card, home equity line of credit, or personal loan from a family member). That kind of money keeps you in the bootstrap trap. OPM is money that is invested in your business and does not put your personal finances at risk.

If you choose option 3, you owe it to yourself to commit and do what it takes to get that funding!

If you choose to raise funding for your business, learn about all the options for doing that.

There are numerous ways to bring in outside funding for your business.  It is not necessary to be a high growth tech startup to raise funding from investors.  Be sure you understand all the options so you can choose the one that fits your business best.

Create your plan.

Spending some time up front to create a well thought out plan will save you time, effort, and regrets on your fundraising journey.  You need to customize your plan to your particular goals, projections, and values so that you don’t waste time chasing funding sources that are not a good fit for you or, even worse, get funding that requires you to sacrifice what you love the most about your business.

We want to help you get clarity on your path for escaping the bootstrap trap.  We are offering a limited number of sessions with our team members who can help you pinpoint your strategy.  To schedule a complimentary session, click here.