We succeeded at inventing the smartwatch and an entirely new product category. The product itself is amazing, people still use it to this day. I personally still use my Pebble 2 HR every single day and I wouldn’t trade it for any other smartwatch on the market.But in the end, we failed to create a sustainable, profitable business. We sold parts of our business to Fitbit at the end of 2016.
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The underlying problem was that we shifted from making something we knew people wanted, to making an ill-defined product that we hoped people wanted.
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Startup founder lesson learned — never forget to define and talk about your long term vision for the future. When things are going well, it’s easy to get caught up in growth. But you need this to carry your company through hard times.Looking back with hindsight, I should not have aggressively grown the company without a stronger plan. We should have just stuck to what we knew best and continued to build quirky, fun smartwatches for hackers.
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A startup is always cycling from lows to highs. The trick is to stay alive between local minima and maxima.
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- funding, entrepreneurship, startups, processed,
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We basically dropped units into Best Buy and Amazon and expected them to sell accordingly. We didn’t do any of the standard practices like synchronizing a campaign across all channels or building a strong influencer network. We struggled with making strong decisions on marketing (and sticking to them) and wavered on hiring a head of marketing for years, before making a decision in early 2015.
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Pebble Time included our new timeline-based operating system that let you perform short, quick interactions (checking weather, calendar, sports, Uber) on your Pebble. We figured this would give us competitive differentiation from sports focused wearables and be useful for a broader set of users. While this software was certainly useful and made sense in the context of a watch, it was exceedingly difficult to explain why customers should care. It failed the ‘make something people want’ test. It was cool and some people used it a lot, but ‘I want my smartwatch to be more efficient’ was not a widespread hair on fire problem. We didn’t do our product research, we didn’t talk to enough of our users.
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The industrial design was good, but it looked a lot more like a playful, colourful geeky watch than a productivity machine. There was a big mismatch between positioning and physical appearance.
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Not only did we not have a clear understanding of our target customer that was shared across hardware, software, and marketing, I think we allowed early success (KS1 and even to some extent KS2) to mask the fact that we never gained a good understanding of what our actual customers valued the most. We lucked into having made something people wanted (the original Pebble) and, IMO, never really were able to figure out exactly why it was successful. So it was hard to reproduce that success.
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Don’t grow OPEX unless your revenue continues to grow. Duh. Seems obvious but still I screwed this up.Losing profitability didn’t help, but probably wasn’t the biggest problem. I got onto the VC fundraising treadmill without really acknowledging it, and didn’t create a fundraising strategy to support us.Market positioning. We forgot the cardinal YC rule: talk to customers. Build something people want. In 2015, we had the option to narrow our focus to a smaller but more distinct market positioning. Looking back, this is one of my biggest regrets. We could have been the smartwatch for hackers but we tried to grow our volumes and market share (and failed).
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But our main issue was that I did a terrible job at defining our long-term vision
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- vision, strategy,

My personal vision was that Pebble would become a brain-computer interface company, with the smartwatch as the first always-on, always-worn gateway between computers and our bodies. But I rarely discussed this with the team, or even the exec team. My rationalization for not talking about this more, I think, was that this would distract us from the many tasks and problems we had at hand of just making and selling smartwatches.I never invested time in building out a structured plan to actually make the brain-computer interface our company’s vision. It never guided our product development. We didn’t talk to customers about problems they had in this space. We never trained or hired engineers to pursue research in the space. It was never in our pitch decks to investors. Every so often it would come up in passing but when colleagues inevitably found holes with the logic I just moved on and focused on tasks at hand instead of trying to address concerns and improve the idea.
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