5 Uncomfortable Things I Tell Every Start-Up to do so they Don’t Start-Down.

4 min readMar 26, 2020

Crazy days we live in, but sometimes that triggers some semi-deep thoughts. For instance, the other day, I was texting with a pal (who happens to be a venture guy at a firm that rhymes with Hey, Sock), and we were sharing a laugh over The Uncomfortable, a collection of “deliberately inconvenient” from the mind of the architect Katerina Kamprani.

Being the predictable fellows that we are, the conversation shifted to why most start-ups fall far from their original ambitions. When design and features overtake function and purpose. Were there actions one could take to keep a fledgling company on target? To first understand and then fulfill its brand promise? How could you avoid making an app that looked pretty but had no utility? You know, just your standard Tuesday evening discourse (hey, this is San Francisco).

For my part, I pointed to a few things I try to impress on founders and their ilk. Things they should be doing, like right now. Not meant to be an exact science, but definitely meant to push and prod in uncomfortable and uneasy ways, the idea is to set the foundations for a brand ecosystem that is clear, authentic and coveted.

Looks good, don’t work so good.
  1. Fight For The Why. I’m no venture capitalist but I’m convinced the last thing these silicon prophets care about is the “why” behind a company. The origin story. The reason for being. What makes you different and more importantly, why should we care? Just having a good product idea or identifying a problem isn’t enough. I’m glad that you worked at Google or Uber, but that’s not really your own brand, is it? You can’t just say you are different and better, you have to be able to show it. Your brand permeates everything. Having a clear understanding of what you are — and are not — will direct everything from your grand strategy to public communications to company culture and office layout.
  2. Hire a P.T. Barnum. Not every founder was born to sell. I don’t necessarily mean someone who can get on the phone and close a deal (or for that matter has to worry about a commission) but someone who can sell the vision and the magic of the brand and story, as if it was a part of life you didn’t know you were missing until now. The companies that I’ve seen truly succeed — and by that I mean lure and keep customers and turn them into brand evangelists themselves — have someone who exemplifies and exudes the brand’s best ambitions and emotions. This person should most certainly be a marketing leader, but one that’s ready to be in the trenches, interacting and connecting with customers and followers eight days a week as if they were running for mayor.
  3. Practice Slow Growth. Out of the 4 start-ups I talked with last week, all four are desperately trying to hire people with titles that include User Acquisition, Growth or Marketing Analytics. The trouble is, all four of these companies are still working on building out their actual products or services, to the point where none of them are really seeing any sort of unforced repeat or return behavior. At Yelp, I remember Jeremy Stoppelman backing up my focus on quality over quantity when he said something like, “I’d rather have 2 or 3 really robust cities and communities than 15 mediocre ones.” This was back in 2006, and I still appreciate his commitment to creating a brand and product that delighted a strong few before appealing to the teeming masses. Metrics are important, but you don’t need analytics to know if your first dozen or so customers are happy or not.
  4. Build In Humanity. There are so many ways to show you care, within the product but also across any medium and touchpoint. Some of the basics I stress are: A) having a personality for your brand in every form of communication B) giving your employees the power to engage in meaningful ways; c) not just posting content but actively participating on social channels; and d) reaching out to individual customers (happy and not) with the express purpose of delighting them. As an investor in six restaurants in San Francisco, I can promise you that the stuff on your plate is just one part of the overall experience; there’s a reason you want to go to a place where “they’re always glad you came.” And yes, I get that this is hard but that’s why you hopefully listened to me on Step 2.
  5. Perpetually Benchmark. In every investor deck, there is always the page about the current competition and market share, and how this latest start-up is going to disrupt the sh*t out everything. I always find this small thinking, at least in terms of creating and establishing an authentic and different brand. You’ve got to compare yourself creatively to really see the vision. Pepsi doesn’t just worry about beating Coke; they think about water, beer, and thirst in general. When I conceived of the Yelp Elite Squad, I borrowed from American Express, my favorite wine clubs in Napa and Sonoma, and the very act of Robert DeNiro entering exclusive eateries in New York City via the kitchen.

Are there more things that matter, and matter more? Can you get by without listening to me? Perhaps. But I do know this: I’ve consulted, advised and met with hundreds of early to mid-stage companies over the last 10 years and when I see the above 5 things ignored (or even glossed over), I sadly know I’m most likely witnessing a soon-to-be start-down, rather than an up-and-coming start-up.