From Harvard Law to Startup Founder: The Real Truth About VC & Bootstrapping

In this episode of Small Biz Tips, we sit down with Khadijah, a former Harvard Law graduate who walked away from a high-paying legal career and built a successful business starting from a simple Google Sheet.

She shares her real journey from being a lawyer to becoming a founder, how she built a platform supporting Black-owned businesses, how she monetized it, scaled it, and eventually exited while still owning 100% of the company.

We also go deep into:

Why quitting can be the smartest move
How to bootstrap a business without investors
The truth about venture capital, seed, Series A, Series B
Why most businesses should NOT raise VC
The difference between tech startups and traditional businesses
How to think about growth, scaling, and funding the smart way

If you are an entrepreneur, startup founder, or thinking about leaving your 9–5 to build something of your own, this episode will change how you think about business, money, and success.

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Keywords
Harvard lawyer quits
from lawyer to entrepreneur
bootstrap a startup without investors
venture capital explained simply
founder story podcast
How to start a business from scratch
black woman entrepreneur story
startup funding series a b c
Quit your job, start a business
tech startup vs traditional business

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Timestamps
0:00 Intro
00:01:28 – Welcome & introducing Khadijah
00:05:42 – Harvard lawyer quits: “My biggest advice in life is to quit.”
00:06:23 – Why staying in a career you hate is worse than quitting
00:07:49 – The Google Sheet that turned into a million-dollar business
00:09:24 – Building a directory of Black-owned businesses
00:10:45 – How a side project became a real company
00:14:41 – Subscription box success story
00:15:22 – Why most people should NOT raise venture capital
00:21:49 – Restaurant vs tech business: why some scale and some don’t
00:29:25 – “Nobody becomes a billionaire by being a good person.”
00:36:19 – Why she invests only in Black founders
00:45:34 – The startup that lets you take an eye exam from your bed
00:50:04 – Why some VC-backed brands collapse
00:50:56 – How people can invest in her fund (minimum $20k)
00:51:39 – How capital calls work in VC funds

#entrepreneurship #startup #smallbusiness #venturecapital #bootstrapping #businesspodcast #founderstory #blackbusiness #startuplife #businessmotivation