$100k Mistakes Zero, Warning Signs: Contracts, Contractors, and the Legal Risks Flying Under Your Radar
• Workshop Room 1
You clicked "I Agree." You paid the 1099s. You signed the contracts w/out reading them. The IRS doesn't care. All are $100K mistakes waiting to happen. Aisha Jorge Massengill gives you 30 minutes to fix what the IRS won't forgive.
Presented by:
Aisha Jorge Massengill Sedgwick Andrews Legal & Consulting
Aisha Jorge Massengill grew up at the intersection of the Sedgwick Housing Project and Andrews Avenue in the Bronx — and she has spent her career turning that foundation into fuel. From becoming the first student in Phillips Academy’s history to earn 12 varsity letters, to earning her B.A. and J.D. from Boston College and her L.L.M. from Georgetown University Law Center, Aisha has always played to win.
With more than 25 years of experience in employment law and business counsel, she has advised large corporations, nonprofits, startups, and entrepreneurs at every stage of growth. She has been in-house counsel. She h
Aisha Jorge Massengill grew up at the intersection of the Sedgwick Housing Project and Andrews Avenue in the Bronx — and she has spent her career turning that foundation into fuel. From becoming the first student in Phillips Academy’s history to earn 12 varsity letters, to earning her B.A. and J.D. from Boston College and her L.L.M. from Georgetown University Law Center, Aisha has always played to win.
With more than 25 years of experience in employment law and business counsel, she has advised large corporations, nonprofits, startups, and entrepreneurs at every stage of growth. She has been in-house counsel. She has been the small business owner. She understands the pressure from every angle — and that perspective is her superpower.
Aisha founded Sedgwick Andrews Legal & Consulting, LLC to give growing businesses what they deserve but rarely get: experienced, proactive legal counsel without the shock of hourly billing. Through subscription and flat-fee models, she serves entrepreneurs and small business owners across Maryland, Virginia, Pennsylvania, Ohio, and Georgia in employment law, contracts, trademark registration, LLC formation, workplace investigations, and general business strategy.
She is also a SHRM-SCP credentialed HR professional, an adjunct professor in Labor and Employment Law, a board member of the American Employment Law Council, and a trustee of Phillips Academy. She has spoken at SXSW, the National Employment Law Council, and beyond — and she actively mentors the next generation of leaders through her work with Bronx to Andover and Back.
Aisha’s message to every entrepreneur in the room is this: legal protection is not a luxury, and it is not something you scramble for after things go wrong. It is a growth strategy — and when you treat it like one, everything changes.
Aisha hosts a weekly podcast on Apple, Spotify and YouTube where she implores small business owners to:
“Build the dream messy, build it scared, just don’t build it small.”