Trust the process

The only failure is failing to learn

Hey there, it’s Tim! 👋 Welcome to The MVP Sprint - my public process of taking HelloHailey from idea to thriving SaaS startup.

I share my metrics, successes, failures, and all the ups and downs of being a bootstrapped solopreneur.

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💪Trust the process

It’s only been two weeks since I soft-launched HelloHailey, and I’m already starting to second-guess myself:

  • Is my MVP good enough?

  • Can a Slack bot really kickstart conversations?

  • Maybe this was a terrible idea…

Positive, negative, and neutral feedback from early users gives me emotional whiplash.

Self-doubt isn’t failure; it’s a predictable side effect of launching early.

I need to trust the process.

I preached this in my second article, but believing it in the moment is much more difficult.


🚀 A soft launch in numbers

I invited the first teams to try out the alpha version of HelloHailey on January 4. Here’s how it’s going:

✉️ 16 teams invited

👩🏻‍💻 8 teams attempted to install

🎉 6 teams successfully installed (2 still waiting for approval)

For teams that installed it:

💀 1 team uninstalled

😍 1 person loved it and referred a friend

👶 4 are still too early for much feedback.

In case you missed my last article, here’s a reminder of what HelloHailey does.

👷‍♂️ Build -> Learn -> Iterate

I need to complete as many (build —> learn —> iterate) feedback loops as I can, as quickly as I can.

I built and launched my MVP in about two weeks.

I've already learned and iterated on a few things:

Hailey’s introduction is overwhelming

She sends a gif and a few messages when she is added to a channel. I spaced out these messages and shrunk the gif.

Gifs are too big

Most messages include a relevant gif. These gifs were too large to auto-expand in Slack, so I made them smaller.

Red tape

Some companies have a lot of red tape around installing Slack apps; some have very little or none at all. In the short-term, I’ll focus my attention on the latter.

❓Small improvements are great, but I need to focus on my core hypothesis:

My top priority is proving or disproving this core hypothesis. My feedback loops need to be pointed towards this north star.

To prove or disprove my it as quickly as possible, I need more users, more time, and more experiments.

👩🏻‍💻 More users

My waitlist has grown to 87 users. I’ll invite 20 new users each of the next two weeks, starting with the earliest sign-ups first.

More users = more data points = faster (and more reliable) learning.

For my emotional sanity, it’s important to manage expectations; I don’t expect all 40 to follow through. Out of those 40 invitations, I’m guessing:

🤐 20 won’t respond.

😫 4 will try to install, but will get held up by corporate red tape.

🤗 6 will respond enthusiastically, but will need a few follow-ups over multiple weeks until they actually do it.

🥳 10 will install successfully within a few days.

Since a lot of you have been following my journey for a couple months now, I’ll let a few of you skip the line!

🎉 The first three readers that respond to this email will get a link to add Hailey to their Slack workspace.

🕐 More time

My pace of learning is slow.

I learn when Hailey sends messages, and she can only send so many messages without getting annoying. Right now she sends one per day.

I’ll counteract this by testing lots of things in parallel.

🧪 More experiments

I’m optimizing for the number of messages in conversations (P1) and the number of users that participate (P2).

An experiment is a product change that will (hopefully) move me closer to those goals.

I’m currently running experiments that test engagement with different types of messages:

  1. Contests - best photo matching a specific theme, funniest photo caption

  2. Social mini-games - ex. Two truths and a lie

  3. “Controversial” statements - ex. Change my mind! Hot dogs are sandwiches…

  4. Icebreakers - ex. “Share your WFH setup!”

  5. Food videos - solicit comments on recipe videos from Tasty.

These experiments will help me iterate on Hailey’s messages. More importantly, they help me get to the root how teammates want to socialize.

Messages are only step one. The insights I’m gathering will help me evolve into entirely new ways for teammates to connect.

🎮 Introducing gamification

When deciding what to build next, I went back to my “How Might I…” questions:

I decided to focus my energy on the third question. I’m going to incentivize engagement with social mini-games and prizes.

Here’s why I think it will work:

  1. Other products use it successfully - Apps like Goals and Hey Taco drive engagement by awarding points that can be redeemed for prizes.

  2. Teams are already doing it - Multiple people I talked to said their companies award prizes for winners of weekly photo sharing contests.

  3. Personal experience - We’ve all seen how a bit of friendly competition can incentivize behavior.

The next two-week sprint is all about defining and building this next product experiment.

What will it look like?

I’ll share all the details in my next update.

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