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Less Annoying Business: Should free trials require a credit card?

published2 months ago
6 min read

Hey Reader,

Tyler from Less Annoying Business here. Here's what's new:

New content

The thing about requiring credit cards to sign up for a free trial [Blog post]
I give my take on whether or not software companies should require leads to enter a credit card before starting a free trial.

Tools don't solve problems [Podcast]
This episode, we've got a grab bag of different topics including a product-led growth discussion, what to do with a stagnent content site, and the role tools should play in running a business.

Mission, Vision, and Values [Podcast]
This episode, we talk about how to define the purpose and constraints of a business.

What I'm working on


Rule #1: Don't innovate

I recently started a new push at LACRM related to growth, and specifically demand generation. This isn't something we normally spend a lot of time on (historically, the demand has generated itself) so it's a bit outside our wheelhouse. When I first met with Alex and Eunice (the growth team) about this, I put a constraint on them: Don't innovate.

What I meant by this is that we're currently pretty bad at demand generation, but there are many people in the world who are good at it. We have competitors with worse products, higher prices, less happy customers, etc. but who still manage to grow faster than us. We aren't trying to do something radical and new, we're just trying to catch up to what pretty much every other successful SaaS company is already doing. There should be no need to innovate. This is about execution. If we're thinking about doing something and there's not already a playbook written by someone else, we simply shouldn't do it. Not yet anyway.

I think this applies to a lot of different areas in business and life. If you read my post on innovation tokens, you know that I don't think you should innovate on too many things. The corollary to that for project where you shouldn't innovate, it's a safe bet that someone else has already figured it out, so the first step is to learn from them. It's tempting to start wildly swinging in the darkness, and that's often the right approach when you are innovating, but that's a terrible approach for things where you're just trying to catch up to the status quo.

Sometimes you need to hit the reset button

Recently, the LACRM team has been feeling a bit misaligned on most of the non-core work we do. By "non-core" I mean the stuff that isn't related to building, selling, and supporting CRM software for small businesses.

We decided long ago that we wouldn't be a "maximize shareholder value" type of business. We care about other things including employee happiness, St. Louis (the city we're based in), D&I (diversity and inclusion), the environment, etc. But I learned recently that different people within the company had different ideas on the role we should play in each of those areas. I had a pretty clear picture in my head, but that wasn't shared across the company.

Misalignments like this have happened a handful of times throughout the history of the company. Every time, it comes down to one issue: A lack of communication on my part. One of the most tedious responsibilities of a CEO is saying the same thing over and over again. When I'm doing my job properly, there's no room for any confusion about anything we're doing as a company because I'm over-explaining it all constantly and repetitively.

But when I fail to do that, people end up filling in the blanks themselves. One person interprets our commitment to St. Louis to mean "we should keep our office here" and another person thinks it means "whatever the biggest issue facing St. Louis is, that should be our top priority as a company". Even though we're all on the same team, we're sort of pointing in different directions. If you let that go unchecked, people will start moving in those different directions and end up in totally different places.

In situations like this, I've found it's best to hit the reset button. What I mean by that, is you need to pull everyone back to the same spot, point them all in the same direction, and set some rules of engagement moving forward. I just did this last week. I gave a presentation to the whole team walking through the history of the company which explained how and why we cared about various things beyond our core business. Then I set some constraints going forward: Sure, we care about these things, but it can't be our job to solve all of the world's problems.

This can be a bit painful for both sides of the conversation. It requires me to be more assertive and restrictive than normal. It requires employees to reset their expectations which is especially tough when it comes to things that they care deeply about. But at the end of the day, everyone is much better off than they would be if we let the misalignment fester. I actually think it's a good thing to go through this periodically because it reminds everyone that like all relationships, our internal team relationships require maintenance.

There's still work to do, but I think we're in a much healthier place now. I just need to remember to communicate regularly about all the stuff I just said in my presentation, or else we'll need to do this all over again in a few years.

Good stuff on the internet

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Dare Obasanjo
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@Carnage4Life
April 2nd 2022
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This is a fascinating point. Over the last ~40 years, we've seen *major* technological innovation which naturally created huge economic opportunity. But over the last few years, things have felt different.

One of the reasons for that might be that we hit a natural limit on the size of the market. Each innovation wave in my lifetime brought tech to an order of magnitude more people. But now, most people on earth have a supercomputer in their pocket. There isn't another order of magnitude left to grow.

This sort of explains what's going on with web3, and to a lesser extent things like VR and the metaverse. People desperately want to be a part of something as big as personal computing, the internet, mobile, or SaaS. So they're trying to will the next major tech wave into existence. But not only are none of the current ideas likely to be as transformative as the past waves, there may never be another wave like that again.

That doesn't mean there will be no more innovation or that people won't find new economic opportunities. Technology will continue to advance, and I'm sure life will continue to get better and better (at least in some ways). But it'll feel different because the total size of the market (as measured by the total number of customers) can't really get much bigger. I feel bad for aspiring technologists who want to get in on the ground floor of something big. The reality is that they probably need to reconsider what "big" means these days.

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Marco Rogers
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@polotek
April 11th 2022
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If you're a regular reader, you're probably sick of hearing my contrarian take on remote work, but this is a great example of something that's been on my mind lately. I keep hearing people act like remote work can absolutely replace everything everyone gets from in-person work with no sacrifices at all. That's so obviously wrong.

You can argue that remote is net better. That whatever you lose in personal relationships is made up for by not having to commute multiple hours every day and being able to find talent anywhere in the world. That's a very compelling argument that I mostly agree with.

But you can't act like nothing is lost. For most people, in-person interactions are just different. The relationships are more complete and fulfilling. You wouldn't want to raise your kids over Zoom calls. Why not? Because IT'S NOT THE SAME! That's also true with your work relationships. I'm 100% behind people that prefer remote work, but only if they're willing to acknowledge that there are tradeoffs, and what's right for one person might not be right for another.

-Tyler