Josh Lowy

A great product won’t be able to compensate for friction in the business model.


Josh Lowy is the co-founder and CEO of Hugo, a note-taking collaborative solution for meetings. Native to Australia and based in San Francisco, Lowy was previously a product manager at Westfield Retail Solutions where he was responsible for building wayfinding solutions for brands to convert online consumer intent into offline purchases.

Where did the idea for your company come from?

Hugo was born out of solving a problem for ourselves while we were facing challenges building a different product. At the time, we were focused on meetings, but the solution revolved around meeting preparation for individuals.

Solving problems as a team is really important, especially as a startup when the tempo of iteration is critical.

But we really struggled to agree as a team on what our customers’ most pressing problems were and why our current product wasn’t hitting on enough of a pain-point. This internal misalignment created a lot of drag for us. So we agreed to build a proof of concept (POC) into the product that posted meeting notes to a Slack channel, and allowed us to create Trello cards from those notes to connect conversations to tickets.

This was a turning point for us in two ways – first of all the team started to create better solutions for our users once they were tapped directly into the firehose of feedback. Something that was a costly, top-down process where the founders had to aggregate insights and share them with the team each week, transformed into a bottom-up approach. This dramatically increased the quality and tempo of our work. The second wave of change was when users started to respond really positively to our hack and wanted it for themselves.

We realized that the problem wasn’t with meeting preparation, it was with pushing information from a meeting to the right people and the tools they use to get things done.

So we faced this as a team:

Option A: keep heading in to the wind and try find an audience willing to pay for our meeting preparation product; or

Option B: Recognize the customer pull on this hack we’ve built, and double down on getting this into the market for teams (not individuals)

Obviously, we chose the latter!

What does your typical day look like and how do you make it productive?

My week is generally organized into two halves. The first half of the week, I work with the team on product development – preparing sprints for the engineers and planning what we are building next. During the second half of the week, I work more closely with Darren (my co-founder) on business development matters, working with information from customers, companies and partnerships. I target strategic opportunities and influencer events to help Hugo earn exposure.

To make each day productive, I do everything I can to reduce the cost of reactive tasks. Managing customers and a team means context switching is inevitable and I can’t always be in control of my time, which can make it hard to get thoughtful work done.

So I get into the office early. I read my newsletters/blogs, stay on top of my email and get a few hours of work done. By the time the team gets in, I’ve cleared a large portion off my plate and can be available for them and our customers.

How do you bring ideas to life?

At Hugo, idea formation isn’t attributed to a single person. I would never take credit as the primary generator of solutions. Instead, we operate as an idea meritocracy, where everyone on the team provides input on solutions and the outcome is always the result of collective input.

Each Monday, we have a product meeting where we discuss challenges that we need to prioritize. Since each team member has a different world view, this open-ended conversation enables everyone to contribute input. I’ll often come to this meeting with some solutions to suggest, but the process of poking and prodding from everyone else is what surfaces the best way forward.

What’s one trend that excites you?

I came to the tech sector from a non-tech background. In the past few years, there’s been an explosion of innovation in business models regarding the role of customer success. Just take a look at the recent market boom of SaaS businesses. Prior to SaaS, many enterprise software companies were maintaining their customers through disingenuous methods like multi-year contracts or by holding data hostage. Now, with such fierce competition, the impetus is on the vendors to show better value by helping customers succeed versus lining their own coffers. The trend of trying to help customers meet their own business goals, as a retention strategy, is exciting.

What is one habit of yours that makes you more productive as an entrepreneur?

I schedule time to think on my own terms. My habit of setting aside a few hours every morning helps me be productive because, like in any business, it can be hard to solve problems if you’re always being reactive and pulled in different directions by your team or customers. Scheduling time, when no one can bother you, gives you space to think about problems without interruption.

What advice would you give your younger self?

When building Hugo, we started out with a different product and had to completely change direction when we realized that we were trying to solve a problem in the wrong way. My advice to my younger self would be to do more validation on the business model, and to not over index on product development in the early stages.

A great product won’t be able to compensate for friction on the business model.

Tell us something that’s true that almost nobody agrees with you on.

I’m not a robot, I swear!

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Optimize our team to run the OODA Loop as fast as possible – Air Force Colonel (ret) John Boyd created the air-to-air combat training methodology called the OODA loop, short for Observe, Orient, Decide, Act. I find it extremely applicable to building a business from the ground-up: Rapid decision-making, lot’s of unknowns, externalities changing frequently and an inability to stand still.

As a team we follow its general framework in two ways:

Holding strong views: We act aggressively as if our view of the world is correct, but discard those views if new information indicates we’re wrong.

But with weak ties: We respond to feedback and new information as quickly as possible, making change if information indicates we were wrong.

What is one strategy that has helped you grow your business?

At Hugo, we have a strong product but initially lacked on the marketing and distribution side of things (getting in front of the right people). At the same time, we were restricted from a cash standpoint. We had to figure out how to get in front of large audiences without spending capital. To grow on a limited budget, we put our effort into developing integrations with larger companies like Slack and Atlassian. Since these bigger players have massive audiences, we are able to get exposed to more customers via their ecosystem marketing, while we focus on continuing to create a great product.

What is one failure you had as an entrepreneur, and how did you overcome it?

When we first started, we were a meeting-preparation product. It quickly became clear that we had to completely change gears. We did so by going back to first principles, examining what wasn’t working and figuring out how we were going to deal with the problem. We went out and talked to as many customers as possible, then explored what needed to change. In the end, we completely threw out our old product and started again from scratch. Through real grit from the team, we created Hugo as it is today.

What is one business idea that you’re willing to give away to our readers?

If you try and ride two horses, you’re sure to fall off both. Right now, I only think about Hugo.

What is the best $100 you recently spent? What and why?

I use Superhuman to manage my inbox. It’s an email product that has changed the way I work and really streamlined my ability to be effective.

What is one piece of software or a web service that helps you be productive? How do you use it?

At Hugo, we rely heavily on Intercom messenger, a customer messaging platform that enables you to talk with customers in real-time.

When it comes to customer support in the product, we have clear data that shows how likely a customer is to be sticky if you can get them to respond to an issue in <5min. For us, the customers who engage the most in support chat, are the most likely to stick with the product and we wouldn’t be able to do this without Intercom messenger.

In the early days, we would not have made it without intercom. I still believe this dynamic holds true for our new customers today.

What is the one book that you recommend our community should read and why?

“Antifragile” by Nassim Nicholas Taleb. It provides a great framework for thinking about grit, and making decisions with imperfect information – both as an individual and for the sake of business.

Embrace hardship, but manage the dosage so that you can grow without breaking!

What is your favorite quote?

“If it was easy, someone else would have done it”

Key learnings:

  • Schedule time when no one can bother you so you have a mental space to think about problems without interruptions and context-switching.
  • When faced with a decision, remember the acronym OODA (Observe, Orient, Decide, Act). Indecision is always a bad outcome, so keep running that loop to keep your errors small and tempo high!