My mother always said he had massive hair on his shoulders from carrying blocks of ice up the stoops of Brooklyn. As I grew up, I began to doubt that ice causes hair to grow, but I never doubted my grandfather’s strength.
We lived in the ground floor apartment of a three-story limestone (a cheaper version of a brownstone) on East 26th between Avenue D and Clarendon Road, in Flatbush, in Brooklyn. My grandfather owned the building (as he did several others around the neighborhood).
Dominic (no “k”) Guido, I believed, could do anything. I knew it ‘cause of the rats.

One day, as I was passing through the areaway under the stoop and getting my purple Stingray bike out of the shed to go for a ride, I saw this nose poking through a wall. “Rat!” I screamed and ran out. An hour later, Grandpa showed up. He stuffed the hole with steel wool and broken glass and patched the hole with cement. Rat problem solved. He could do anything.
He also remains to this day my ideal entrepreneur.
He’d left school after the sixth grade. He’d come to America from Palo del Colle in Bari and starting with nothing but a pushcart, he built a mini-empire of two or three trucks (and three or four buildings) selling ice in the summer and coal in the winter (and homemade illegal wine all year long during Prohibition).
He’d made enough money to raise seven kids (some of whom even went to college). And, most important, at the end of the day he always had more money than he had at the start.
I’ve met thousands of entrepreneurs over the years. I get the mindset. I’ve been there, done that; I’ve struggled, celebrated, laughed, and mourned with dozens of them. And when I was an investor, the ones who reminded me the most of my grandfather were the ones I was quickest to fund.
I thought of him, with his gnarled hands, suspenders, perpetually rough cheeks the other day when I was meeting with D.
“At least,” started my client, “at least I can say I raised a lot of money.”
Really? I thought. What would Dominic say?
I get that fund-raising is hard. It’s probably the most frequent topic in my sessions with CEOs. I also remember vividly sitting on a board of a company as it struggled to raise its next round.
But I also remember another client—T. T’s worked at his business for nearly four years. He’s built his business selling his software product one customer at a time. This year, he’ll clear $300,000 in revenue and be able to pay himself livable if not great wage as well as the salaries of a developer, a business/sales jack-of-all-trades, and a representative in the UK.
And he has no debt. And he owns 100% of the equity in his company.
Clearly not all companies can be built this way. And clearly, too, T’s business might be able to accelerate rapidly if it had a decent infusion of cash—if for nothing else than to improve his SEO ranking.
Nevertheless, there’s something sweetly endearing about the hand-built, boot-strapped business…something that Dominic would appreciate.
Grandpa’s Rules of Business
1) Debt? What’s Debt?
2) Always have a secondary income plan. Sell ice but don’t be afraid to sell a little wine as well.
3) A nap in the middle of the day is a good thing. A nap at the movies in the middle of the day is a very good thing
4) Figs are best when eaten right from the tree
5) Chicks dig Old Spice
6) Don’t take off your long underwear until the spring.
7) When in doubt, go ahead and buy the extra truck
8) Find out what your customer needs and sell it to them
9) Work harder than your competition
10) Laugh
11) Eat lemon drops
12) Families are good; big families are better
13) Always remember who you are and where you came from
14) Always have more money at the end of the day than at the beginning.


