Investing in IfUIWill

Every now and then a very smart guy who I have known a very long time calls me up with a crazy new idea they are working on. I love these calls and am humbled when they call me first. This happened a couple weeks ago when my longtime friend (and former Microsoft colleague) Peter Mansour gave me a ring from Majorca. The Universe (ok Instagram/Twitter) connected the dots as he is passionate about solving a problem I have been very public needs solving. After a couple of weeks of digging into his traction, team, product approach, and market entry strategy, I am happy to be leading the Pre-Seed in IfUIWill .

IfUIWill: Do Together.

The Story

This may come as a surprise to you, but I struggle with getting everything I want to do done. Even when I start off well with something, the weight of distractions can pull me in all directions. This is especially true for new habits, learning something new, or anything that requires a commitment over time. The most effective method I have found for sticking to commitments over time has been the challenge framework, especially with your friends. I have tried a bunch of different systems for this and even invested in a few (@Spar) but have always found them limited in some way (one type of challenge, work stuff only, lack of integrations, etc.). When I was running Upgrade Labs, we wanted to sponsor a sleep challenge integrated with Oura. It took us over a month of custom program development to create our own challenge. I have influencer friends who run challenges for their audiences with custom mash ups of Shopify, Instagram, GumRoad, Excel, YouTube and bailing wire. While people love challenges and organizations see amazing engagement with them, all this one-off development creates a lot of friction. Why hadn’t anyone created a software platform optimized for multiple challenge types across multiple categories, especially one which could scale to the Enterprise? I wanted this so badly, I toyed with doing it myself, even hiring a CTO to do some scoping work. And then Peter called me.

Peter and I worked together at Microsoft and again after I left and started Tippr while he was running Local Offers and Coupons as GPM of Bing Local. in 2017 Peter moved to Majorca to be Chief Product Officer at Hotelbeds Group. We shared our favorite bike rides there as Majorca is on of my all time favorite road bike places. We also enjoyed trading start-up ideas. Peter likes having interesting problems to solve like I do. He got interested in challenges after doing a couple fitness challenges on the internet and being frustrated by the tools. He decided to build a better one, one that he would love to use himself. Peter launched version 1.0 of the IfUIWill app in Nov. of 2019 and worked iteratively with early adopters. The app has now been used by thousands and is on version 4.7, all bootstrapped with his own resources.

The current consumer product makes creating and managing any kind of challenge fun and easy. Peter had tried @SPAR (where I am an investor) and was frustrated, like me, with the fact that it only supports one use case – The kind where you agree to pay money if you don’t complete the daily video checkins. There are many other challenge formats which don’t include daily checkins or require fines. One of their most engaged early customers was PAWSwalk which challenges you to walk your dog daily and compete others on hours and miles walked. By supporting flexible challenge design and accountability, IfUIWill is building a more generalized platform which can address a much larger set of use cases. They have built templates for the most common challenge formats and are adding more. This reminds me alot of how Survey Monkey took the general idea of a forms generator and used a common back-end infrastructure to support multiple us cases from academic research, to audience surveys, to contact forms and more. Much of the one-off integrations I had to build at Upgrade Labs to make my own challenge, are now baked into the IfUIWill platform saving me tons of development time. Shared back-end infrastructure with multiple front-end low variable use cases, that is the essence of a great Platform.

A couple months ago, Enterprise customers started calling and asking Peter if the platform could be used for employee engagement and meeting internal goals around health, wellness, training, etc. While they have plans to monetize the consumer app, Peter always felt the real monetization would be in the Enterprise. He knew going to the Enterprise would require significant scaling up, so he gave me a call.

One reason I put out to the Universe problems I want solutions for is that every now and then, you get something back. Someone else is as passionate about the problem and is going to off and solve it. I am excited to be leading this scaling round with Peter.

Why I am Investing

Peter is solving a problem I have been looking to solve for some time. I know him and his execution abilities well. Peter has has been a start up CEO before and has experience in multiple big tech companies. He has gotten a very long way on his own and is ready to scale into the Enterprise. Very excited to be the first check in as lead.

Trends I am betting on

Remote is the new normal. Regardless of the pandemic, we are going to have less in person time across all areas of our lives than before. Connection with those we don’t see every day has become more important than ever. Challenges are a great way to stay connected and stay in community with people around the world.

Competition and community drive goal achievement. When I am the only one looking at my to-do list, it can get stale. When I am in a community, that accountability keeps everyone on track to a much higher degree. People are 65 percent more likely to meet a goal after committing to another person. Chances increase to 95 percent when they have partners to check in on their progress. This trend also drove my investment in UNLU where their class completion rate was 2X Masterclass due to the community aspect of their platform.

Why this deal is Incisive

IfUIWill ranks very highly in key areas of our Meta Themes.

Great Founders figure shit out. Peter is a second time founder with an impressive track record from big tech companies as well. Having managed large teams, he understands the value of employee engagement and has a great network of HR managers as potential customers. He has shipped over 100 versions of the application in the last 10 months, responding to user feedback, pivoting, and building value. He knows how to refine product/market fit.

Disruptive Innovation creates new Markets. How big was the forms generator market before Survey Monkey? or ride share before Uber? How big can the challenges market be if there is a simple scalable platform that makes it easy for anyone to create and manage challenges? With the reduction in challenge friction enabled by the platform, I believe at least 100x larger.

Platforms Win. Custom software development sucks. Build once, use many wins. Challenges are stitched together today mostly with duct tape and bailing wire. In the early days of any feature there is a lot of coding. But today web sites are build by builder platforms (WordPress, etc.) not by hand. A challenge platform will create and drive the demand and use of challenges faster than every possible before.

Invest with other smart people. The other angels in the round are also long time friends of Peter and have had impressive careers as operators and investors. I am excited to partner with this group of people.

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