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Sheryl Hunter, Esquire: Be Sure That You Really Need a Partner or Investor

Updated: Jul 19, 2020

In this episode we talk to Sheryl Hunter of Hunter Business Law - The Entrepreneur’s Law Firm. We opened with "Are Partnerships and Investors Like Marriages?" Then we step through Sheryl’s backstory from Georgetown Law to big corporate and ultimately starting her own firm dedicated to entrepreneurs. Among other topics, we talk about the biggest and most common legal setbacks and derails she sees with entrepreneurs, partners, and investors - and how to avoid them.

SPONSOR: Executive Launch ( – from corporate executive to startup founder

Full Episode (YouTube):

0:10 - Are partnership or investor breakups worse than marriage breakups? Sheryl says they definitely can be and we discuss how risky it can be going into business with a friend or family member. Just because you know someone well in a social setting doesn’t mean you know them well in a high pressure business setting.

4:42 - Check personalities - are you more likely to say ‘Let’s make our best guess and go!” or “Let’s not go until we know!”? People’s thought processes and work styles can vary dramatically and it isn’t clear until tested in business. Allen says ‘go camping’ with your prospective partner.

8:15 - Are you more likely to say “A penny saved is a penny earned” or “you have to spend money to make money”. And then there’s the ‘idea person’ and the ‘doer person’.

10:37 - SPONSOR: Executive Launch ( - from corporate executive to startup founder. Sheryl reinforces the difference between corporate decision-making and startup decision-making. Example executive-to-founder: Salesforce, Peoplesoft, Zoom, etc.

16:15 - Grew up in Illinois & Indiana. Competitive golfer, tennis, skiing, named her daughter Aspen. George Washington U as undergrad - no attorneys in family, no plans to be an attorney.

18:25 - Internship at a state attorney's office - inspired to be an attorney to help people. Went back to DC and Georgetown Law.

21:06 - Joined large law firm, great firm. They did a lot of pro bono, she worked on the battered women's clemency project. But something didn’t square for Sheryl, that voice inside.

24:27 - Made move to a small specialty firm - Nursing Home Abuse Law Center, helping our most vulnerable.

25:47 - Allen’s book Quit to Start - Why would you leave a big secure job with a big firm?

26:54 - Then a big leap, started firm with a partner. Having worked at a large firm and then a small firm, gave her the foundation, and experiences needed.

29:22 - If you’re young and switching jobs every few years, use an extra lens to envision how you would do it as an entrepreneur yourself - perhaps you will one day. And develop your personal professional brand.

37:35 - Then Sheryl made the biggest leap to start her own firm that she runs today - Hunter Business Law ( Combining law and business, 360-degree business viewpoint with clients. Tiny office to start but was able to build her client base quickly, years of relationships and experience paid off.

49:20 - Building a profitable services company is a solid path, you are building something of value that you can sell one day if you choose. Building do-or-die tech products can often leave you with no value if not a home run.

51:53 - How did you find clients in a niche market? Existing relationships but also - gave talks, free content, entrepreneurs afternoon teas - being generous with time, volunteering. Can’t see how to have a 40 hour work week as an entrepreneur.

56:05 - Advice to founders with investors: transparency & over-communication. Investors can be helpful now but more importantly, later.

1:01:18 - Advice in partnerships. Control disputes - they can lock the gears of a business. Best to have a prenup agreement - and have an advisory board to help decision log-jams.

1:03:14 - The Money Man (non-operational investor partner) and The Worker Bee (non-monied operational partner) - important to keep the working partner motivated. If you’re doing well, increase rewards and possibly equity for the worker bee partner. Partner agreements: equity, control, & comp.

1:06:35 - When company is struggling, still need executive motivation. Investors are more likely to be fair and reasonable if you’ve been communicating.

1:11:58 - Key question to a business owner or starter - are you sure you need a partner? Collaboration is important, but do you need a business partner for that?

1:16:00 - Do you really need an investor? Many founders say they wish they hadn’t. You’ve worked hard to be your own boss - then you wake up and realize you have a boss, your investor(s). Look closely at the alternatives.

1:22:30 - Sheryl’s passion projects relate to women’s issues. GirlTalkShop - happy hour for women to talk business. GEMS ( - Girls Empowered Mentally for Success. And, founder of Liberty Law Suites, co-working and accelerator for attorneys.

Hunter Business Law:

Full Episode (YouTube):


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