I will delve into the nuts and bolts of why Pineapple ultimately didn’t succeed from my own view, below but if you are reading this, you were probably in some way associated with us, be it as an investor, an employee, a community member, or even a fellow founder (hi Dave). I want to take this opportunity to truly thank all of you. It was a great experience, and I have immense pride in the work we did at Pineapple. Pineapple started out as a simple idea, an itch I had to scratch. I often found myself going back to that original idea, looking at the app in awe of how far it came, but now acknowledging that it didn’t go as far as I had hoped or dreamt. So to each and every one of you, thank you so so much for helping me dream a little!
It’s not meant to end this way, but it so often does - it’s funny how these brain dumps from the founder are far more common than exits themselves but much less discussed. There is a learning within that itself.
My key learnings - these are things I will take with me into my next venture as the huge lessons
Market Pull - we were sitting in one or bi-weekly meetings with F7 and I couldn’t quite find the words or phrase for what was going wrong with our growth, Kelly Graziadei interjected and asked we’re we not seeing market pull - there it was in a very simplistic statement, which neatly summarised a number of years of pain. Quite frankly the market didn’t want what we were building. Simple as, I have made peace with that! I think you can have good or bad problems, by that I mean ones with are fixable and ones which aren’t, trying to create market demand for something that would ultimately require millions of daily users to be a truly viable entity is in the latter set of those problems. We discovered this the hard and painful way, my key learning from all this and advice to any other founder is try to establish the market pull for your platform as early as you can, if it’s not there move on quickly. Something we should have done!
Blinded by our vision - as a founder for a business that ultimately didn’t succeed, I feel it's crucial to take my share of the blame. Looking back objectively over the last number of months, I acknowledge that I was blinded by the idea of Pineapple, the hope of it, if you will. This led me to overlook obvious signs of it not working, mostly from a metrics/growth point of view.
Being a founder presents a challenge when you're trying to keep the team and investors on board. You leverage signs of hope to keep them motivated, which you also sell to yourself. It's extremely hard to be objective and tell yourself it's not working, but that's the job. In hindsight, we should have pivoted far earlier. We had the fundamentals (more on that below) to build something of value, but the core concept or our approach to it was flawed.
Tailwinds - I came across an interesting tweet that stated the likelihood of another major social app breaking through in the next five years is less than 1%. It made me realize that the consumer-social game has largely been won, making our challenge that little bit harder. In an already incredibly tough game, you want to give yourself every fighting chance.
When I mention tailwinds, I think about industries or fields like Bitcoin over the last number of years and now AI where the winner has still to be crowned. While it doesn't fix all your issues, but it certainly does help to benefit from the tailwinds of a larger trend and the associated macro benefits. Unfortunately, we didn’t have them to leverage.
Mission focused - While we were extremely mission-focused as a company, which I believe is important, I think we honed in on our solution to the mission rather than examining the overall mission itself. We assumed what we were building was the solution to professional networking for Gen-Z. While I still believe there to be an opportunity in this somewhere, I think we should have approached it with a blank canvas of an idea, rather than forcing our visual stories onto them as the core solution to professional networking being broken for the next generation.
With the rise of professional Discord groups and career influencers on TikTok, the next generation does have a strong interest in professional topics. I believe what we built with Pineapple was an evolution of professional networking when a revolution was what was needed. For anyone looking to build in this space, feel free to reach out to me; I'm happy to chat.
What went well - things I look back on with immense pride!
Founder and Team Fit - I genuinely believe we had a very strong team, especially at our peak when we had a well-rounded, solid core of 7. Small to most, but we were nimble, driven, and, most importantly, we clicked for a period. Myself and Dave always had a great dynamic, thankfully, which probably made harder conversations about the concept not working even more challenging. The culture and overall team dynamic were there; we just didn’t get the traction from the market to drive us to the next level.
When I mentioned we had the fundamentals to succeed above, this is what I mean. I would have loved to work on something that was truly growing with this team - we could have done great things together. We had great ideas and great execution, both from a product and marketing lens, but it was misplaced. The quote below from Robert Green sums up the team's situation. This isn’t to say the team ever ran out of energy or interest, although I often did, but when you don’t get the love from the market your output deserves, it's hard to continuously perform at a high level.
You could have the most brilliant mind, teeming with knowledge and ideas, but if you choose the wrong subject or problem to attack, you can run out of energy or interest
Robert Green, the Daily Laws.
Investors - We were blessed when it came to our investors, and I genuinely mean it. Often, it's considered a cliche or a box-ticking exercise when founders express gratitude for their investors in these notes, but our experience was truly exceptional. In terms of the VC’s, we had an amazing relationship with Tim Chae in 500 Global, who possesses one of the best minds I have ever come across. He provided clarity when myself and Dave didn’t have it and never gave up on us. Kelly and Joanna were truly very supportive; they are relatively new to the VC world, and you could tell they really wanted to create a firm that went above and beyond for their founders.
We also had some great angels, who were often my closet of friends. They supported me both when it was going well and when it wasn't. I am forever grateful to any of my friends who jumped in with me and didn't even blink when I told them it was over. ❤️
What didn’t go so well - I think these were some of the mistakes we made and what I would change
Growth - When you state market pull not being there as the core reason for its failure, it's clear that growth didn’t go well. This is something I still battle with internally: was the demand not there, or did we not find it? I am leaning more into the 'it wasn’t there' camp. However, I do think as a team, we never truly owned growth. We weren’t scrappy enough, we weren’t creative enough. Don't get me wrong; we tried and tried, but maybe we could have been better.
When I say "we," I was chiefly in charge of growth, and this is something I must take with me into my next venture. I think market pull can make you look like a great marketer and growth hacker, but ultimately when it doesn’t exist, or more so, you don’t find it, it reflects badly on the growth side of the business.