Bootstrapping or VC Funding?

I’ve bootstrapped and raised VC money. Here’s how I funded each of my 3 businesses:

Business #1 - Bootstrapping
My first business was completely bootstrapped. It was easy to do with a boutique consulting firm. It started with just me, then I gradually added a tiny team. I scaled myself to only focus on landing sales with large insurers, while the team led initiatives we were hired for. I owned 100% of my business. This business did not have any venture risk.

Business #2 - Bootstrapping + $30M in Venture Capital
Second business was a tech startup that started bootstrapped - just me and Microsoft Access. After 6 months I brought on a co-founder and an engineer that lived in India. We joined the Techstars NYC accelerator program.

I raised $30M over 4 years, scaling it to $28M in annual recurring revenue. I raised money from VC's, angels, friends, family and banks. We used convertible notes, term sheets, credit lines and venture debt to scale.

I owned 13% of my business but was making a bet that it would have a massive outcome. To work, we needed to get to 1M customers before the insurers took us down. It was exactly what VCs look for. It had venture risk in a highly regulated market with a proven way to acquire customers fast.

Business #3 - Bootstrapping + Angel $$ + Customer Funded
Using what I learned from both of my previous companies, I bootstrapped to start. I raised a small angel round using a SAFE. It has venture risk, but this time I'm not taking money from VC's quite yet. Instead I'm focusing on being customer funded and profitable.

Our scrappiness got us to profitability within 3 months of launching. This gave us leverage on who we take money from as we scale. I own 84% of my business.