It’s Thanksgiving today, and we’ve got much to be thankful for. If you celebrate this holiday, may it be a relaxing one spent with family and friends.

But this is a business publication primarily about our investments, so here’s the story of Crayon.

The Crayon home page.

Mike and I have both known Crayon’s cofounder and CEO, Jonah Lopin, for a long time. We worked together at HubSpot for years, going through the startup ups-and-downs, and dealing with different issues as a team, growing together.

When Jonah and his cofounder John originally started Crayon, they built a “marketing inspiration” product, Crayon Inspire. In this…


I don’t like phone calls, and I’m not alone: increasingly, Americans, and especially millennials, avoid the phone.

Of all the phone interactions, customer service is near the worst. Phone trees are hard to navigate, and can take a while, even before you’re put on hold with bad music while waiting for the “next available” agent.

What if you didn’t have to wait? What if you could express you problem easily on a web page, and someone took care of it for you automatically?

GetHuman solves this problem, and does it well.


tl;dr: I want to build innovative products that positively and directly impact many people. I’ll still do angel investing, especially with my friend Mike Volpe in Operator.vc, but going to focus on building high-impact products for now.

For the last two months, since leaving Jana, I’ve been exploring the venture capital (VC) career path. This post contains some of my thoughts and reflections on the topic. It’s a bit lengthy, hence the summary above.

Much of this is personal. Much of this is also more of a passion-driven decision, as opposed to right vs wrong or good vs bad. …


This post explains why I invested in QuikForce, a “moving as a service” company based here in Boston, long before it had a product or any traction.

From www.QuikForce.com

I don’t think this would have been a long post anyhow, but the co-founder and CEO of QuikForce, Desmond Lim, made this post even shorter when he published “Entrepreneurship Lessons From My 18-year-old Self” a couple of days ago.

Please go read Desmond’s post above. Then tell me you wouldn’t invest in this founder :) It’s an easy call.

I first met Desmond while I was working at Jana. As a product person…


A few weeks ago, my friend Mike Volpe came up with the idea for GrowthCamp, a practical one-day growth hacking conference for the Boston startup ecosystem.

From “What is Growth Hacking?” on duraid.me.

I’m excited about this, will attend and help make it happen. Here’s how this is different from most conferences, in no particular order:

  1. Practical. Theory has its place, often well-covered in books and blogs. But if I take time out of work to attend a conference, I like its content to be immediately useful. …


Yesterday I had several meetings, but two of them had a common element worth discussing.

Namely: both companies had young engineers serving as heads of engineers. In both cases, these guys are doing a great job, not only building their product but growing their teams, working with non-technical folks and other stakeholders, and more.

From “Go and Rust: The road ahead for two young programming languages” on InfoWorld.

In one case, the company was started while the team, including this CTO, was still in college. In the second case, the head tech guy joined after about a couple of years of professional experience in a big company.

Both companies are doing great, growing fast…


I’ll start with a quote from Fred Wilson, a venture capitalist at Union Square Ventures:

“No business is so good that the wrong people can’t mess it up. And no business is so bad that the right people can’t fix it…so if you don’t get the people part of the equation right, everything else is really immaterial.”

To date, I’ve mostly invested in companies before they have a real (if any) product or traction in the market. In this context, one is betting on the team even more than in other, later, stages when additional data are available.

The internet…


Almost every startup I advise or invested in needs help with recruiting technical talent, the people who build products.

I can (and probably will) write several posts on this topic. But here’s one very concrete, easy tip you can use to help your technical recruiting. I call this the “suits to hoodies ratio.”

When considering how to find engineers, spend your time at low “suits to hoodies ratio” events / locations / activities.

(Or, alternatively, a high “hoodies to suits ratio.”) The more suits, the worse your odds.

To be clear: I’m using “suits” and “hoodies” to represent roles or…


Today is a big day for WeFunder, which was one of my first startup investments, and other companies active in that “startup crowdfunding” space.

This is the first in a series of posts about investments I’ve made, explaining some of my thinking, as well as reflecting on things I’ve learned since. If you have thoughts on format, contents, etc on these posts, please let me know.

First thing first: I’m a tiny investor in WeFunder. I was part of an early angel round, and I’m happy with my investment. This post explains why.

Today is a big day for the…


Meta: this is the first post in a series I’m doing by request. In each post, we’ll take a look at one pitch deck and tear it down. What we like, don’t like, what’s missing, and why. These are more art than science, there’s no fixed right or wrong, but hopefully the discussion is helpful to entrepreneurs building their own decks. Comments, requests, etc all very welcome!

Reid Hoffman, who was early on at PayPal (part of that awesome “mafia,” the likes of which I’d love to see more in Boston, but that’s another future post), then co-founded LinkedIn, and…

Yoav Shapira

Serial entrepreneur, advisor, and investor. Built and ran product, engineering @CarGurus, @HubSpot, @Happier, @Jana. Now working on Well-being @Instagram.

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