I’m now finally in a place where I can move fast again.

I’ve just hit a major milestone, in that what I casually tell friends has been the “one and half years of misery” finally came to an end at 17:30 last Friday, when I pushed the payments system live. (One thing I’ve not learnt in a decade: don’t push things live on Friday evening!).

The payments system is somewhat mundane in & of itself, but it represents something much greater: the final step of an almost complete revamp of everything ActiveInbox.

The tl;dr is I’m finally looking forwards, rather than inwards, and freshly enabled to finish some things for you that I’ve been thinking about – and prototyping, and gathering feedback on – for 3 years.

A more thorough review

The longer version, if you’re inclined to read it, will be my attempt to share some honest insight into what’s been happening in the company, and the impact that has had, and will have, on ActiveInbox.

It’s probably mostly of interest to fellow indie hacking / bootstrapped startup geeks, but I hope it’s also interesting enough to skim for anyone who wants to know the personal story behind ActiveInbox.

The big beats of ActiveInbox’s history

  • 2006
    I built ‘GTD Gmail’ for myself, as a way to do simple ticketing in Gmail, for a startup I co-founded back then. Without any fanfare, I dropped it into the public domain, just in case some other people thought it interesting.
  • 2010
    I finally incorporated “The Inbox Foundry Ltd” as a vehicle to support what was now ActiveInbox. In the intervening years, I’d failed at the first startup (ironically made irrelevant by Google), joined another on the rebound, but all the while, ActiveInbox was getting written up in magazines and drawing donations ($20,000 from about 700 people). It just took me a while to realise the little side project was in fact the real thing.
  • 2011
    Made my first and most enduring hire: Lisa took customer support, releasing me to focus more on product, but making sure customer’s needs were actually heard loud & clear.
  • 2010-2012
    We had unsolicited interest from investors, and even Google reached out to figure out a working relationship. I was very comfortable being a boutique product maker, and didn’t want to disrupt that, so we kept going as bootstrapped. We had a rich community who guided what ActiveInbox became, with me as the main maker, some very talented helpers, serving a group of passionate customers. It was an intensely fulfilling time.
  • 2010-2015
    Lots of competitors sprang up (Paul Graham, of the influential incubator Y Combinator, had declared “email tasks” to be the 2nd largest startup opportunity on the entire internet). That competition included Google, with the launch of their Inbox app, which was dangerously close in concept to ActiveInbox. That was a deeply traumatic surprise at the time, but in retrospect is one of 4 “events that should have killed us” that didn’t. Because competitors never do outright. It takes a more internal failing to do that (and I’d argue that description characterises the next 5 years…).
  • 2015
    In reaction to competition, decided to “grow up”. Which meant moving beyond my core of building product, and in retrospect, marked on a loss of focus on constantly pushing the product forward. Hired our first full time positions for marketing, sales and development, and took a loan to hire an amazing team on contract to build a mobile app, including a designer who probably created the longest lasting impact in dramatically beautifying ActiveInbox.
  • 2015-2018
    Realising that the intense competition, and our low price, meant marketing had become almost prohibitively expensive, we returned to our “safe space” roots as product makers. The great hope being to innovate some big new idea that would break through the noise. But unlike in 2006, I felt I had some reputation to lose by releasing something sub-standard, which led to lots of ideation but a hesitation to actually release things.
  • 2018-2020
    Paddling hard just to keep our head above water. With our growth plateaued, and therefore already a drop in confidence about the future, we were hit with two “Act of God” style events. First, Google released a dramatically different Gmail. It took 8 months for me to do a very rapid rewrite of ActiveInbox to work with it, negatively affecting ActiveInbox’s stability in that period, which – very understandably – led to losing customers. Second, after that rewrite, Google got spooked about security, requiring us to find (in a period of contracting sales) “$15,000-$75,000 per year” to undergo a security audit. It wasn’t just the financial fee, it was the cost of essentially having to rewrite ActiveInbox a second time to ensure we’d truly become world class at security (which we did: more on that in a bit).

    This post is drawing a line under that tough period, to relay how I’ll be going forward, and to let you know I’m still dedicated to being a boutique product maker, building ActiveInbox for you (but with a plan to build a more robust company to support it).

With one indisputable positive North Star

This post is really about identifying strategic mistakes that I want to correct, and so naturally overlooks what was successful. Very simply, we’ve lasted a long time by software company standards. We’ve served an audience of very successful customers (we attract a lot of executives, entrepreneurs, leaders) for 14 years, and I’m primarily proud that we did it in harmony with you all as a community, invested in making something that really helps productivity. (I’ve spent 1000s of hours on Skype calls with 100s of you over the years.)

Identifying failures that have let you down

The turn of a decade is interesting. Rather than another New Years of “last year had some bad bits, maybe I’ll fix next year”, the recurring lies one tells oneself become much clearer over 10 years.

In order of severity, those problems distilled down to:

  1. Never choosing where to excel
    I never committed to focusing ActiveInbox on solving one customer problem, for one group of customers. This is the core of almost every other problem. The temptation to be everything to everyone (and also not to push away any customers who supported us from the early days), with the remote possibility of a big win, was too great, and I think mainly ego-driven. It left us competing against the broad mission of Google to boost productivity, without Google’s financial resources to do so. The most serious problem this caused was paralysis: it was hard to release new powerful features that would have delighted one group, but increased “bloat” for another, so I hesitated to release anything.
  2. Insufficient revenue
    We never raised prices. Again, in wanting to be “for everyone”, we had to keep prices at the lowest common denominator. So even though we had more than 10,000 customers, we never had the resources to really deliver as quickly and robustly as I think you needed.
  3. Holding back creating a more rounded team
    I resisted making the tremendously talented people who I got to work with, who brought complimentary skills, a meaningful part of the company. This was mainly a lack of commitment from me (I never truly resolved whether I wanted this to be a fulfilling product that brought in a good income and time for a great lifestyle; or to deeply invest in creating a mature company that other people could bet their families on). If I’m brutally honest about myself, there was also a lack of maturity in sharing my role and potential upside, especially having spent the early years as a solo founder (aka the sunk-cost fallacy in psychology). The other lesson I should mention is I definitely suffered the egotistic belief I must learn a skill before I could credibly hire and manage for it; instead of hiring a genuine expert would have been instant in results, more educational, and require less management.

    On a personal note, as a social person, this ‘problem’ is probably my biggest actual regret of them all, even if it isn’t the biggest cause of failure: because not having an equal to bounce ideas off and share the strife, and not having a culture where we tried and won as a team, made the whole endeavour a less human experience.
  4. Choosing short term gambles over long term safe returns
    In times of stress I have a tendency to return to my safe space of making the product better, instead of pushing into sales, marketing, or any other discipline that wasn’t my area of primary expertise. Essentially a common failing amongst indie product makers is looking for a “big breakthrough/shortcut” with new products, rather than making steady progress. I can really see this “tortoise & hare” situation in retrospect: had I been more disciplined in growing out different skills across a team over 14 years, even if it was only slow progress, there’s a good chance we’d have much more capability to deliver right now.
  5. Getting slower as time goes on
    A consequence of the short-termist thinking of #4, technical debt was allowed to balloon over the years (“tech debt” is where the code has become so complex and intertwined that a feature that should take 2 days to complete ends up taking 2 weeks).
    Solo founders are also prone to not re-evaluating the problem/solution landscape rigorously enough (primarily as there’s no one to create discussion tension with), and there’s definitely been an under-current of wanting to make the solution fit the concept I arrived on in the 2000s, rather than stay open to changing problems and technologies. The dissonance created by wanting to stick to a concept while also exploring new frontiers ultimately achieved neither, and led to decision paralysis.
    Combined with the Acts of God above, and a fear driven attempt to protect my reputation, it’s meant that nothing that stands out has been released for at least two years.

I basically failed to align the scope of problems you wanted me to solve with the resources to do it. I should have committed to either taking on investment and talent to step up, or shrunk the scale of the ambition down and planned to expand over the long term.

Making the changes for growth

Already achieved

As much as the last couple of years have been painful, they’ve resulted in a few major positives:

  1. I can move fast again, as the technical debt built over the last 10 years has been cleared. It no longer takes a whole team to achieve absolutely anything. ActiveInbox has a clean modern codebase, and all 4 of our servers are written in the same language, with the same system, and hosted on Heroku (who handle almost all of the maintenance work).
  2. Our security and privacy is world class, which is the most important objective in handling your email. (It’s a small glimmer of pride, but we actually went above & beyond what was required for the Security Audit, and the primary technical expert for Google-appointed security firm who penetration tested us sent a text to a colleague stating “this client is doing an awesome job… wish there were more software teams like this”).
  3. I’ve conducted umpteen customer interviews, and built multiple prototypes, for new features in the last few years. They’re now ready to be composed and presented to you!

Focusing on a single, clear problem to solve

Rather than give you a glib sales line, I want to show you my thought process for the problem I want to solve.

At a very high level, there are a few global trends that make success harder for us as individuals:

  • With rapid advances in technology (and more to come from AI), it’s not expected we’ll have a career/skill for life. We’re going to have to simultaneously maintain jobs while redeveloping ourselves to stay relevant for employment.
  • A proliferation of new software tools, and of course our phones, mean we’re “always on” and open to interruption.
  • The internet, which promised to empower us all with a voice, has instead helped a few corporations scale out to unprecedented global power, negatively impacting the leverage we have over our careers. Similarly, despite remote working becoming technically possible, in order to benefit from professional networks, we have to concentrate ourselves in high priced cities. Both of these things combine to put financial pressure upon us, and mental pressure to work harder.

So, at a time when we need to have the headspace to be strategic with our careers, and build our professional network; we’re getting increasingly bombarded, squeezed and frazzled.

There are a few more insights that feed into how it might be helped, in our small realm of email:

  • What’s very cool, and oft overlooked about email: it’s open to the entire world. You don’t need permission to connect with absolutely anyone, and from those connections spring new opportunities.
  • But it is a double edged sword: the openness means it’s awash with noise and interruption from absolutely anywhere. And email clients, as a simple chronological list of letters, are dreadful at protecting our headspace. McKinsey found it takes up 30% of an average knowledge worker’s day.
  • That noise is why it’s hard to get anyone to reply – even close colleagues – because they’re too overwhelmed in their own inboxes.

Drilling down further into the highly specific problems of email that need solving:

  • Be able to focus on deep work, by reducing the number of interruptions and tasks in email. (This is essentially what ActiveInbox does, by grouping many little email tasks into contextually related batches, and making it easy to come back to them later, so essentially 10 related items become one task.)
  • Get more replies, quicker, by reducing the burden on the recipient.
  • Be confident time isn’t wasted in email, and that you maintain a great reputation with your contacts by replying in a timely manner, by adding business analytics to the black-hole of today’s email.

The core of this is I want to make it easier to connect with people through email, to take advantage of opportunities that spring up, by reducing the email overload for both sender and recipient. I’m not just solving reducing time in our own inboxes, but reducing time in inboxes across the network. To a large extent this will be achieved by acknowledging how we as senders have a lot of responsibility in respecting the recipient.

The primary audience will continue to be executives and managerial (CxOs, entrepreneurs, partners); but I anticipate testing to see how well it works for outbound (sales/PR) teams as well.

(As an aside, another major problem to solve is adding collaboration to email, to better serve a customer, or make decisions about a product feature issue, by pulling together all siloed information trapped in email out into a shared view, available to everyone to contribute or utilise. But for foreseeable, this is outside the scope of that core remit)

Building a delivery machine for you

The immediate goals are:

  • Increase cashflow
    To accelerate how fast I can build and serve.
  • Find a partner, a possible co-founder
    In particular to compensate for my main weaknesses. Someone who actually enjoys detail and rigour, ideally with experience in demand generation marketing & running sales. While I’d love a co-founder, given the difficulty in settling in with someone I’ve only just met, at first I’d be happy for a mentor to provide the scaffolding of this role.
  • Validate the problem-to-solve above
    It needs to be much more concrete than that description above, for which I will be interviewing you and releasing mini products.

To actually do that, the roadmap is:

  • Raise prices for ActiveInbox
    It’s long overdue, as we’re about half the price of our nearest competitor. If you’re already a customer, we’ll grand-father your current price, as I’m acutely aware you’ve supported ActiveInbox to this stage.
  • Keep supporting, and listening to feedback, on ActiveInbox
    I just want to make it explicit, I’m moving forward, but ActiveInbox is coming along for the ride.
  • Work in a more entrepreneurial environment
    At present, I work with fellow product makers and tech geeks (and often from home), but it will be great to be amongst people with complimentary skills.
  • Get on the phone for sales calls for the new solutions
    The primary goal here is to fully validate and pick a single priority for the new problem-solutions I’ve been brainstorming, but it also needs to bring a cash boost (until now, my calls have been with existing customers to discover your problems, but there wasn’t any focus on fresh revenue).
  • Build a team of equals
    To compensate for my deficiencies, first an experienced-product-orientated-entrepreneur mentor in the next few months, then the most talented people I can find to fulfil engineering, sales and marketing.

I’m still at my happiest being a boutique product maker, talking to you, listening to your needs, and crafting fresh and transformative solutions.

There are broadly 3 types of motivation for an entrepreneur: impact, money and experience. I’m definitely the former. ActiveInbox, and the sibling that will be joining it, will continue to be built with a mindset of serving you for the long term.

But, the big change is to commit the next decade to building a company that can keep doing so with much more resilience, and pace, than we’ve had.

Thank you for all the support you’ve given ActiveInbox over the last 14 years, that’s got it to where it is today.


This was written by Andy Mitchell