5 Lessons I Learned When I Created My App or SAAS: “Real relationships matter” with Darren Chait…

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5 Lessons I Learned When I Created My App or SAAS: “Real relationships matter” with Darren Chait and Mitch Russo

Real relationships matter. Many of our greatest wins have come off the back of genuine relationships we’ve built here. People at partner companies, other founders and random Uber Pool passengers have all led to our early learnings and growth to date. This is no surprise, but I’ve absolutely learnt the value of optimizing for real relationships — not superficial network relationships.

As part of my series about the “5 Lessons I Learned When I Created My App or SAAS”, I had the pleasure of interviewing Darren Chait of Hugo. Native to Australia and based in San Francisco, Darren Chait leads the growth and operations side of Hugo. Solving some of the pain around meetings is a cause close to Darren’s heart. Prior to founding Hugo, he was a lawyer at one of Australia’s largest law firms — he attended meetings for a living! Sharing his frustration with a close friend, now co-founder, the two decided to build Hugo to re-think meetings based on the new way that we work. Today, Darren regularly writes and speaks at leading events about trends in the way we work and the impact that SaaS is having on teams. He and the Hugo team are on a mission to reconnect the way we meet to the way we work — for themselves and the thousands of teams powered by Hugo. Darren earned his Bachelor’s degrees in Commerce and Law — at the University of New South Wales and a Graduate Diploma of Legal Practice from the College of Law.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’m one of two co-founders of Hugo, based in San Francisco. I grew up in Sydney, Australia and worked there as a lawyer for a few years before making the jump to start Hugo in the US.

In retrospect it’s kind of funny I ended up in corporate law. I’ve always had the ‘entrepreneurial bug’. Through high school and college I had a mobile DJ business with a school friend — we played at hundreds and hundreds of parties over a few years — and I was always dreaming up different business ideas and tech-savvy ways to create value where opportunity existed.

It took a close friend who I had worked with in a non-profit setting to push me to join him and build Hugo — responding to a frustration with meetings that we both shared in the professional world.

What was the “Aha Moment” that led you to think of the idea for your current company? Can you share that story with us?

There was an interesting trend we observed. So much was changing about how we worked — remote was becoming the norm, the explosion of SaaS and so many different tools used by the average organization and the disappearance of hierarchy and centralized decision making. But, at the same time, nothing had changed about the way we meet. People need to carve out huge chunks of their day to join a forum of unprepared colleagues who spend time updating everyone on what they were doing, have a few minutes of discussion and debate and religiously write notes and agreed actions which typically go nowhere. If you weren’t in the room, you aren’t in the know and all this valuable knowledge is lost.

We wanted to connect the new way we work to the way we meet. Interestingly, we went about it in a completely different way to how Hugo works today.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

There are so many! When we launched Hugo 1.0, my co-founder and I spent our days in meetings. We were almost always out of the office talking to customers, partners and investors — understanding what we needed to build next and who for.

A divide started forming across our team. We’d come back and debrief what we’d learnt and how it should be translated into our priorities and decision making, but the team couldn’t always understand. They weren’t there and missed out on the discussion, debate and decisions. At the same time, everything Josh and I captured was spread across docs, notebooks and our CRM, impossible to find again and identify trends amongst.

So we did what most tech founders would do. We turned to more tech to solve people problems. Except, it actually worked. We built ourselves a hack with a Slack integration that would ping us for notes after every meeting based on our calendar data. From there it would share the insights to relevant members of the team and organize the notes based on the contacts and companies we were meeting. Soon we realized that the takeaways and actions shouldn’t be bullet points but rather Trello cards and Jira issues, so we built those integrations. Almost overnight our entire team was aligned. It was as if they were in every meeting with us, able to action insights before the meeting was even over!

Funnily enough our customers were more interested in what we had built for ourselves than what we were selling and Hugo 2.0 became Hugo’s Hugo if you know what I mean.

We didn’t consider giving up. There’s something obsessive about solving a problem that you experienced yourself — you can’t stop until it’s fixed. At the same time validation from customers is like fuel to our fire. How could we abandon all these real people who have this real problem and who are not relying on us to be successful? That’s how it feels anyway 🙂

So, how are things going today? How did your grit and resilience lead to your eventual success?

We’re getting there! Growth has been fantastic and today we’re powering teams at great companies all over the world. Grit is the exact word we think about when talking about our experience. It sums up what’s required as you never know whether the next small change or course correction is the one that will lead you to success — you can’t see what’s around the corner.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

Being Australian and moving to the US provides many great stories. The nuanced cultural differences are sometimes hard to spot. I remember feeling so disheartened starting out with sales here in the US. Australian sales culture is very much about longer-term relationship building and ‘slow maybes’. Here, I was getting very direct ‘no’s’ right away, not even a ‘let me think about it’, or ‘sounds interesting, let’s keep in touch’. In retrospect I appreciate that so much more, but it definitely bruised my ego!

What do you think makes your company stand out? Can you share a story?

We’re excited to have a product that has such a direct influence on the way teams work. Creating a meeting culture and instilling values of transparency, openness and voice can have transformative impacts for companies that adopt the Hugo meeting workflow. That’s a unique opportunity which means a lot to us.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I’m certainly not the ideal spokesperson here as I’m still learning these tips on a daily basis. One of the most effective tips for me has been to surround myself with people who can understand what I’m up against but not necessarily in it with me. That way they can remain a relatable sounding board, somewhat removed from the frontline.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

While it sounds cliche, I have to say my co-founder. I don’t know how sole founders do it. It can be a lonely journey and without a cofounder there’s no counterweight for the invariable highs and lows.

Ok thank you for all that. Now let’s shift to the main focus of this interview. Approximately how many users or subscribers does your app or software currently have? Can you share with our readers three of the main steps you’ve taken to build such a large community?

We’re not sharing this at the moment (due to some ongoing investor conversations). One number we’re proud of though is how we’re able to achieve 90 percent penetration in many of our customers. We enter a business through one department (say customer success for example) and spread horizontally until almost the entire organization is onboard. That penetration metric is an important one for our business model.

What is your monetization model? How do you monetize your community of users? Have you considered other monetization options? Why did you not use those?

We have a freemium model. Hugo is free for teams of up to 40, and we charge for 41+ or for some advanced features in smaller teams.

We started with a free trial model, but the nature of Hugo means you need to get started with the meeting workflow to understand the value and create a habit. We found the free trial time constraint got in the way of users getting started and forming good habits, so we switched to freemium.

Based on your experience and success, what are the five most important things one should know before one wants to start an app or a SAAS? Please share a story or an example for each.

1. The obvious one: Solve a real problem for real people (i.e. a big enough market), that they would be willing to pay for. Test this early before you get too deep. Yes, it’s textbook, but it’s true and easy to forget when you’re in the trenches.

2. Focus on your team right away. As a software company, your great idea is nothing until it gets fed to a few smart people who translate it into a product of real value. Creating a great culture, the right processes and alignment is critical from Day 0, as it pays dividends everyday.

3. Distribution is everything. I recently read a great tweet which said ‘First time founders focus on product first. Second time founders focus on distribution’. We learnt this the hard way — how you’re going to get your great product into people’s hands is as important as how great your product is. Work on this early.

4. Pricing matters. There’s so much great content out there to read on pricing. We underestimated the impact that pricing can have on growth and adoption. For example, when we changed our freemium seat-count, we almost doubled the number of daily active users in weeks.

5. Real relationships matter. Many of our greatest wins have come off the back of genuine relationships we’ve built here. People at partner companies, other founders and random Uber Pool passengers have all led to our early learnings and growth to date. This is no surprise, but I’ve absolutely learnt the value of optimizing for real relationships — not superficial network relationships.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

It still blows my mind how many incredible immigrants there are in the US and what they have built and are building. It would be great to see more and more support for those people who have left their families and homes to come here to build something great.

How can our readers follow you on social media?



This was very inspiring. Thank you so much for joining us!

5 Lessons I Learned When I Created My App or SAAS: “Real relationships matter” with Darren Chait… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

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