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Perspectives on entrepreneurship, startups and venture capital from K9 Ventures.

The Story of How/Why K9 Invested in Pragli

Pragli is a virtual office for remote teams that facilitates faster communication and increased closeness between teammates.

Here is a quick video:

It all started with this tweet by Jeff Richards of GGV Capital (@jrichlive) on Twitter:

I happened to see Jeff’s tweet on my timeline and thought to myself: “I have no idea what this company does yet, but I like how they think.” Because, to rent a U-haul, put a banner on it and park yourself in South Park is about as good as it gets for Guerilla Marketing. And obviously it was working because Jeff tweeted it, and I saw it. My inclination was that “this is a team of scrappy founders, and I like how they think.”

I went over to the Pragli website and started exploring. I immediately liked what I saw. It reminded me of something I’ve been anxiously awaiting for many years. The seeds of this were sown decades ago when I was TAing CS147: Introduction to HCI at Stanford with my Ph.D. advisor Prof. Terry Winograd. In CS147 one of the video we showed to the class was the Sun Starfire concept video that was produced in 1994. Yes, 1994!

In the Starfire video Sun envisioned not only the iPad, but an always-on communication tool that allowed teams to always have a sense of presence and also be able to communicate with each other with minimal friction. Even though this is something that has been envisioned for so long ago, none of the current tools, including Slack, or Zoom, had gotten this right. 

Those who are old enough will remember Mirabilis’ ICQ — I can still hear it’s iconic chirp in my head as I type this. Instant Messaging as it was then called had come really close to providing a sense of presence. Today we have some of that in Slack, but desktop instant messaging’s peak has passed us as we’ve moved most of our communication over to the phone.

The Sun Starfire vision was missing one piece though — it felt a little bit invasive when it came to privacy (watch the video). 

For the last two plus years, I have been running a startup, HiHello, as it’s CEO. HiHello has a remote team of engineers – in New York, Pennsylvania, Colorado, and California. Several months ago I was having a conversation with my friend and former co-worker @ HiHello, Leith Abdulla, about how I am frustrated with Slack and want a tool that removes the friction for communication with the remote team. We’d already tried the Zoom integration in Slack, so I could simply do /zoom join me in order to escalate from Slack to a Zoom call, but it still wasn’t as frictionless as I would like. Removing friction for remote teams comes with a combination to presence awareness and instant activation. So I was telling Leith about how there can be a better solution for this. 

For years now, I’ve had a sticky note on my desk which says “MyTeam — always on video” as a reminder to myself that this is something I still want to build/invest in. In fact, the sticky is probably still on my office desk, but I’m at home because of COVID-19 and so couldn’t grab a picture of it for this post!

When I saw what Pragli had built, all the dots started to connect. They had figured out how to do presence without compromising privacy — by using animated avatars. They had reduced the friction to connect by making anyone literally one click away — one click and you open a voice channel to them.They can hear you, but you can’t hear them until they unmute yourself. This little UX default is brilliant, as it simulates a double opt-in, without compromising privacy.

I was so excited to see the Pragli website after Jeff’s tweet that I almost instantly went and followed the company and the founders on Twitter:

At this point I figured that maybe this is a company that has already raised capital and has a 10+ person team. But, I also know that it’s better not to assume, and so I made a mental note to check in with this team. (It was an incredibly busy and stressful time as my father was critically ill and I had to urgently leave for India).

On Tuesday, February 11th, Gabe Hayes who is on our team for HiHello, posted this to our Slack channel:

I was busy preparing for my flight to New Delhi that evening, but Gabe’s slack message reminded me that I wanted to reach out to the Pragli team and so I pinged Doug Safreno, the co-founder of Pragli on Twitter (guessing he had followed me back so that I could DM him):

For the next few days I was in India and hadn’t heard anything back from Doug. As I fought to stay awake waiting for my return flight in the wee hours of the morning at the airport in New Delhi, I figured I’d drop Doug an email:

Doug responded right away and we scheduled to chat once I was back in the US and in the office on Friday, February 21st. By this point almost everyone (with a couple of holdouts) on the HiHello team was already on Pragli and I had used it enough to know that I really liked the product. So of course, we did our first meeting over Pragli.

I was blown away to learn in my first call with Doug that they were a two person team, and had not raised any funding to date. I think the next thing I said to Doug was: “Well, then I/K9 would like to invest.”

But it wasn’t that simple! Doug and his co-founder Vivek Nair, were not planning on raising any venture capital money yet. They had already done one startup before that was venture-backed and they realized that they should only raise venture capital once they are ready.

I invited Doug and Vivek to meet in person at The Kennel the following Tuesday (Feb 25). We met, and I told Doug and Vivek about how I’ve been thinking about this problem for a long time, and I think that what they’ve built is the best solution I’ve seen to date. I also shared some ideas with them on product, pricing, and go-to-market, in the hopes that they would be intrigued enough to let me and K9 invest in the company. Alas Doug and Vivek were determined to not raise capital yet, and so we decided to just stay in touch.

Meanwhile, I continued to use Pragli on a daily basis with the HiHello team. The app had made communicating with the team much more efficient and high bandwidth for me. In fact, I often found that it was easier for me to communicate with a remote colleague on Pragli that it was to even get up and walk to the other room to talk to a co-located colleague! In my mind Pragli had nearly achieved remote-work Nirvana!

Over the next two weeks, the world changed. COVID-19 started to hit the United States and more and more companies started implementing “work-from-home.” The HiHello team went to fully work-from-home on Monday, March, 10th. The same day I sent another follow-up note to Doug and Vivek:

We re-engaged and started talking about Pragli raising capital. I won’t get into the details of our negotiations, but it suffices to say that Doug and Vivek as accomplished founders had multiple options for raising capital even under fast declining market conditions. 

I am pleased that I/K9 Ventures got to lead the Pre-Seed round of financing for Pragli. We didn’t waste any time from signing the term sheet to getting started on working on the company — even before the financing closed, which happened on Thursday, April 2nd.

Over the course of the last several weeks, I’ve had a chance to work closely with Doug and Vivek and I can attest that they are an incredible team. They operate at a pace that far exceeds that of any other companies and founding teams that I have worked with. It’s amazing to see what they have built as a small but super efficient founding team. They are always thoughtful and I am honored that they chose to work with me/K9 for Pragli.

In closing, I’ll thank Jeff Richards @ GGV for his tweet, Gabe Hayes @ HiHello for surfacing and being the first person on the HiHello team to try out Pragli, and the HiHello team for being open to trying new tools to make our communication and collaboration better.

The future of work is remote. I used to rail against remote work, and now I am a convert — because we’re finally getting the tools to make remote collaboration better, sometimes even better than being in the same office.

I hope you all get to try out Pragli — remember that you need to onboard your team that you collaborate with on a daily basis to get the most out of the product.