Don’t Start That Because…

Ideas are easy to kill, but maintaining dogmatic optimism in the face of endless skepticism is the hallmark of any entrepreneur. Here are 8 examples of perseverance now worth trillions of dollars. 
August 31, 2021
Save time with the Jog 👇

The aha moment!

The team was sharing a lot of content with each other and we didn’t have time to consume it. This happens every day: I find something online, I open a chrome tab and then forget about it. There's a goldmine of expert advice available online, yet finding it relies on serendipity. 

You don't invest 2hrs of your life watching a movie without watching the trailer... Why spend 20 minutes reading an article on "optimizing your sales team" if you don't know if it'll be useful? 

We need a place that tells us what's relevant to consume, saves it, reminds us, and, most importantly, saves us time reviewing it. 

I told the team to send the link and a very brief summary: the key ideas. We can decide whether to read more, or use it to jog our memory later.

Launching in 42 days

  • Joggo's TAM is massive. 
  • Content production is increasing rapidly across an  increasing number of channels and it's overwhelming to keep up. 
  • Joggo helps you discover what to consume, and speeds up that consumption, saving you time. 

Once you've experienced content discovery with Joggo, it's a magical experience you won’t want to live without. 


I always believed that I’d start a business, it would grow and I’d become successful overnight. Funny how the world doesn’t work that way. It took me an enormous amount of courage to start a business, by leaving behind a team I built and loved, and a career I enjoyed, but it was always my dream. I couldn’t have forecasted it would take the turns it did, and I couldn’t have predicted a global pandemic would start a few months into the journey. The only certainty was that nothing was certain or going to be as expected, and it was the unknown path that was the journey to be navigated, and most importantly, enjoyed.

I founded Imagine to be the payment network of the future, an attempt at disrupting the monopolistic tyranny of the global financial networks and give power back to merchants to deliver a better, more rewarding experience for their customers. Imagine relied on merchants of all sizes adopting a new technology en-masse and moving fast to do so. As time moved on, it became increasingly clear that this fundamental requirement for us was not materializing, and we needed to change things. After almost 3 years of passionately convincing everyone who’d listen about how Imagine was the future; the music stopped, and it was like running into a brick wall. 

The Pivot 

Our mission had strongly resonated with longtime industry execs, both during initial research and throughout the life of Imagine, but when it came to action, we lost confidence in being able to get the critical mass we needed to break a trillion dollar industry. Merchant priorities were scattered during the first 6 months of COVID as they figured out how to survive, and our product was too complex to consider implementing. 

I analyzed the original hypotheses that needed to be true for success when starting against the current position we were in and the decision to pivot was obvious. It was an emotional decision yet I viewed it as a sunk cost: if it wasn’t working, change it. Most importantly, change it fast. There is a longer story here which I’m happy to share - please reach out directly if you’re struggling with a similar situation and want to talk it through. 

I spoke to each investor individually one on one and was fully transparent - our investors had put their faith in me and the vision I’d laid out, and I was embarrassed to communicate, what I considered to be, a failure to them, but I passionately believe they deserve the unredacted truth. I was humbled by the positive support I received and I am so grateful and proud to call all of them partners. Almost unanimously, their feedback was “go find the next thing you’re passionate about, that’s all that matters”. So that’s what I did.

🚢 Righting the Ship

Pivoting meant we no longer needed the size of team we had and we needed to cut burn to extend runway. This unfortunately meant saying goodbye to team members we liked which made the decision difficult. My advice is to do this swiftly and without hesitation: it’s better for everyone. We were fortunate to eliminate a large amount of overhead across a number of other areas that gave us a relatively clean path forward and our runway doubled to give us time to develop a new direction and find product market fit. 

The reaction from the remaining team was invigorating. The energy level increased by orders of magnitude: you could feel the passion and drive to find a new direction. I executed the pivot on Monday and began working on a new direction on Tuesday. 

We gave ourselves the remaining 5 weeks of the year to ideate, test concepts, and find that passion.

We laid out clear criteria for any new product direction:

  • Our desire to work on the problem for a long time
  • How fast we could get to market with an MVP
  • A product we can quickly get feedback on to improve things fast
  • Small beginnings, big vision: one user finds it valuable, many users find it priceless
  • A clear path to monetization

🎬 Kick Off - A Legal Toolkit

Our initial direction focused on the problem of completing complex deals - specifically anything that required a diligence process e.g., an investment, or an M&A process. This was an area I had experience in and could relate to the problems on a deep level. We interviewed a broad group of over 40 professionals in two weeks - lawyers, bankers, accountants, investors. 

We felt great about the quantity and quality of feedback we were getting and we built a rudimentary prototype in a day as part of a week-long design sprint - see here - to test pre-christmas. Overall product feedback was not unanimous but we got a strong signal about one feature, so we decided to continue for a few weeks, but maintain an open mind on new ideas. 

My wife and I escaped San Francisco for Christmas to spend time with her family in Brazil - much needed after 2020. Big lesson learnt here: take a break every so often as the inspiration pays for the time away and the team is more than capable of filling your shoes. We agreed the engineering team would spend a few weeks elevating the prototype to an interactive experience we could get more feedback on, and I would evaluate other ideas in case the ROI for continuing on the legal toolkit didn’t make sense.

We tested the prototype on Jan 6th and received lukewarm feedback on some fundamental questions - it wasn't clear who our economic buyer would be, and we were concerned about the complexity and the time it would take to build a product with suitable accuracy for a user. We also had lingering concerns about the size of the TAM. 

It was lucky we gave ourselves the openness to explore other ideas because, as this ideation phase rolled on, we identified an interesting problem we were all encountering...

🌟 Aha!

The team spent a large amount of time reading and researching and people would share links of content they'd read/listened to/watched with others as a recommendation of something that would be useful to everyone. 

I realized this happens every day: I find something online, I open a chrome tab and then forget about it. A friend sends me a link, I open it and forget about it. I read something, then rarely save it. If I do save it, I can't find it. There's this goldmine of expert advice available online, yet finding it relies on serendipity, knowing who to follow on Twitter, or opening the first 30 links on Google and spending time reading before knowing if it's what you needed. Or you listen to a 1 hour podcast and don't know if it was useful until you've spent the time. 

This was the “aha! moment💡”. You don't invest 2hrs of your life watching a movie without watching the trailer... Why spend 20 minutes reading an article on "optimizing your sales team" if you don't know if it'll be useful? We need a place that tells us what's relevant to consume, that saves content we want to consume, reminds us about it, and, most importantly, saves us time reviewing it. 

I told the team, don't only share the link with the team. If it takes 20 minutes to read and 5 people read it, that's 100 minutes of time. Send the link and a very brief summary: the key ideas. Then we can decide to spend more time reading it or not. Plus, we can review the key ideas later on to jog our memories on what we read. 

🚀 Let's Go!

Joggo was born. I spent the Christmas break writing up a detailed memo to share with the team and close advisors: there was a clear signal we had something. It's hard to quantify, but it "felt right" - a lightbulb had gone off and there was this great wave of energy being unlocked. People got it immediately. It was effortless to explain. People wanted this. 

We began to focus on Joggo work on Jan 7th. 42 days later, we launched. 

🏗 Our Process

We needed two major components for an MVP...

A compelling product that a user could:

  1. Save links to any content (article, blog, podcast, tweet, video etc) to an online library that can then resurface what they saved to remind them about it later
  2. Organize links into Playlists
  3. Share Playlists with friends
  4. Find experts on topics and view their Playlists
  5. Read a summary (we call it a Jog) of a link before diving in so a user can quickly decide how to spend their time

An initial library of content so:

  1. A user gets value from discovering great content on Joggo before they've saved anything themselves - create the moment of delight as fast as possible with as minimal friction as possible
  2. Crack the chicken and egg problem to get users a reason to come to our site

We identified what the “perfect product” would look like, and then we started cutting. We cut as much as possible until we were left with exactly what we thought we needed for the initial batch of users to get utility from the product. Then we started building fast. We figured we could never get all the answers right, so get the product in the hands of consumers and they’ll tell us what direction to move in next. 

We defined an initial GTM niche:

What jobs are we doing for our users?

  • Discover content
  • Accumulate knowledge
  • Retain more knowledge
  • Share knowledge

Find categories of people with these job requirements

  • Academics
  • Entrepreneurial-types
  • Finance-types
  • Professionals (managers, lawyers, etc)
  • Others such as professional coaches and journalists

What are the desirable traits we’re looking for amongst target users?

  • Disposition - i.e., curiosity, ambition, knowledge-seeking
  • Consume lots of short-form evergreen content
  • Share a lot online
  • Early adopters

We looked at the overlap of traits per category of people and scored them accordingly. The results were clear: the startup ecosystem (tech, VCs and entrepreneurs) was a perfect match so we settled on this.

We went hunting for the best content online for this audience. We scoured social media for what people were sharing. We asked friends to share their personal bookmarks. We mined a huge database of URLs to the very best content available online and threw it all into an Airtable database. Then we thought, ok now what?

A central thesis of Joggo was a great discovery tool combined with summarized content. We realized there’s no way we could summarize the 5,000-6,000 links we had mined with the limited resources we had. We manually sifted through the database and highlighted the 10-20% highest value, highest priority items that we thought were a worthwhile investment to summarize and recruited help. We went to the top schools in the US and found students looking for jobs in these categories. We figured we needed about 5-10 to do roughly 500 pieces but the word kept spreading organically and within 10 days we had 40 signed up, onboarded, and creating summaries - all via word of mouth. This was the first sign that we were on to something and gave us a lot of energy to continue. This initial community turned out to be far more productive than we originally thought and we quickly found ourselves replenishing the priority database. We also found that many wanted to be involved with what we were building so we gathered feedback from them and invited them to start using the product first to kickstart the user feedback loop. 

Our website, waitlist and referral program are live and feedback has been really great.

Where We're Going

Joggo's TAM is massive. The amount of content production is increasing rapidly across an ever increasing number of channels and it's overwhelming to keep up. Joggo not only helps you discover what to consume, it speeds up that consumption, saving you precious time. Once you've experienced content discovery with Joggo, it's a magical experience you won’t want to live without. 

We plan to build Joggo in public so expect more content soon. 

This pivot was not easy: on myself, and on the team. I want to thank everyone who supported us and guided us to the place we’re in now. You know who you are and you have our eternal gratitude. We’re excited to bring this product to life and build on the incredible feedback we have received so far. The future has many unknowns and I’m expecting many more bumps, but this direction feels right, the journey is fun, and we’re excited to bring Joggo to the world.

Get started