Building a company is the hardest thing anyone can ever do

You are surrounded by hanger ons.

The advisor who wants equity for making some (decent) intros. Maybe a (quasi) successful person who thinks they know all of the answers and is excited about your brian child (and wants it to be their hobby). Maybe a “friend” who works at some large company (or even better, investment banking), went to Wharton, and is going to grace you with their (normally bad) advice and promises of capital and some of their oh so precious time (even though they haven’t built a thing and couldn’t operate themselves out a paper bag).

The investor who also hasn’t built anything, takes themselves very seriously, thinks you should be delighted to even be talking to them, has opinions about things they shouldn’t have opinions about, and can’t understand what you are doing unless they use cliche terms to compare it to other things (“so it’s like the Shopify of Furniture with an Uber Market SaaS Network”). I mean, why don’t they get this? You’ve been “too early for them” or “too late for them” or “the timing isn’t right” and why do they even care about the conversion rate in May of 2024 for some model that you pulled out of your ass — don’t they get this? If you were doing $400k of MRR you wouldn’t be speaking to them to begin with.

The Vendors who really want to create all of this value that you cannot afford nor trust. SEO snake oil. PR people who want $12k a month (but it takes a 3 month contract for them to even get out of bed). The financial, planning, and analysis specialist who your board recommended that can take care of your spreadsheeting, and accounting, and admin (but turns out to make things even worse).

The employees who always want a pound of flesh and require leadership. Hello imposter syndrome! The marketing hire who is very good at marketing themselves, costs 10x their big salary in budget, can’t spell LTV, and you don’t know if anything they are doing is going to work for 6 months. The spreadsheet jockey from Business School who’s willing to “come in from the cold and join your startup” for $120k and 10%. The person one of your board members introduced that “could be helpful”.

Keeping people motivated, the business growing and funded, while managing the countless stakeholders is close to impossible.

You can’t go home and tell your life partner what’s going on (they worry).

You can’t tell employees how you feel (they need leadership and job security).

You can’t confide in your board or investors (they react).

Vendors want to be paid and customers want a return.

You are on an island.

I’ve been on that island too.

About Me

MY NAME IS David (I’m the one on the Left)


After founding and running a large SaaS business day to day (ShopKeep); I sit/sat on some great boards (Kickstarter, ShopKeep, Vengo, Amper Music, Gooten, Columbia University's Lang Center); advise many others (Gooroo, BentoBox, Tattle, Wekudo, BarAndClubStats); and spend time at Columbia Business School as Entrepreneur in Residence. Worked in M&A for a bit (NASDAQ: IACI) and helped private equity firms buy companies (PwC). Now helping people build life changing authentic professional relationships full time at Voray while also investing as a venture partner to a well capitalized fund here in NYC (and the occasional personal angel investment).

Authored Failing Forward, a weekly column on venture backed entrepreneurship in Inc. and am a contributor to The Observer.

I have an accounting degree from Tulane University and an MBA from Columbia University.

I love to dive, am not as great a skier as my wife, and have run a few Triathlons as a member of the Michael J Fox Foundation's Team Fox ("run" being really generous). A Certified Public Accountant, born in Brooklyn, I live in Manhattan with my wife and two sons, but regularly visit the borough that's thorough to consume large amounts of corner squares at L&Bs Spumoni Gardens.