Do as I say, not as I do

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Do as I say, not as I do

This phrase is usually said tongue in cheek. Or its said as a defense to preempt the response “but that’s not how you did it”.

Maybe you hate this phrase. If I was hearing it from someone who succeeded doing one thing but was telling me to do another, I would chafe.

But as someone who’s found themselves saying this quite a lot recently, I have a newfound appreciation.

And that’s because I’ve now lived through the consequences of ignoring my own advice. My advice is backed by war stories and mistakes. And when I say it, it comes with the force and sincerity of trying to help the founders I work with avoid the mistakes we made as we’ve built Day One.

So I wanted to do two things. First is to highlight a few examples of advice that I give founders today, that I definitely did not follow, and why it’s so so important to do as I say, not as I do (did).

Second, I want to unpack why we as founders so often ignore the advice given to us (it’s so common that there must be a reason).

But first, let me share the tip of the iceberg of advice that I share today, but did not follow myself.

Three pieces of advice I ignored (and regretted)

Advice #1: Please please please focus on one niche customer

If your target customer / persona / ideal customer profile has an “and” in it… you’re probably targeting too large a group, or worse yet, multiple groups.

When we started Day One, we wanted to support all the entrepreneurs and founders who the VC ecosystem left out… which meant we were focused on “the 99%”. Ladies and gentlemen, let me tell you, there is more than one single customer within the 99% who aren’t being supported by the VC ecosystem today. It’s an awesome mission, but we struggled for years to nail down our core target customer.

I know why this one is hard to implement. You feel your solution is so awesome and you know that it will be valuable and impact all the groups in your way-too-large target market. This may be true… and if each of these customers found their way to your product, they could each get value. But the value would probably look different. So then when you went to post awesome testimonials, any given testimonial would only speak to a subset of our audience. And now when you go to market, you don’t have a good way to target all your customers, or have a single message to pitch them.

Ultimately, this is about your GTM. You can’t build the M part of PMF if you don’t get narrow and niche. I’m pretty sure it’s a universal truth, so ignore it (like we did) at your own peril.

Advice #2 Please please please do not scale your team until you find PMF

And related advice: do not grow your team immediately after fundraising, and do not grow your team “ahead of” demand in the early stages. All three of these pieces of advice roll up to the same thing - the founders of an early stage business need to do all the hard, unscalable things until you reach PMF, and each “thing” (product, marketing, customer success, etc.) has been largely solved by the founder.

I will say, we hired freakin’ awesome people at Day One. Our mission and backing allowed us to build a killer team. But unfortunately, building a team will not help you find PMF, and it will not solve the challenges you haven’t solved yet. In fact, it will make it harder, because finding PMF requires lots of iteration and even pivoting, and getting 6 people to switch direction is a lot harder than 2 or 3.

In hindsight we made all of these mistakes, and it leads to very painful decisions as a founder. You might get lucky and find PMF with the direction you and your growing team are already headed. But not likely. And when it comes time to pivot, you’ll be steering a larger ship, with people who might not be a fit for the new world, with way less cash than if you hadn’t grown.

Advice #3 Please please please think deeply about your business model

And do not just implement a business model because others in your space are doing it. Your business is not their business, and you need to make sure your business model holds water - or better yet, is a competitive advantage - as you build.

We launched Day One during the rapid rise of the Fellowship model. It seemed obvious how to set up the business - run a cohort based program, charge a one-time fee, and keep getting new customers from referrals as the community grows. But that model has flaws - no ongoing revenue, relatively high fees are a drag on growth. We eventually started experimenting on new models, and only this year have we landed on a business model that works for us.

So don’t follow the pack. Instead, you have to do a lot of work on your business model before you scale. Part of what you need to iterate on as you find PMF is your business model - how much you charge, how you charge, who you charge, all make a huge difference. Don’t let this be an afterthought

So why do we ignore good advice?

I don’t think it’s anyone’s fault that most good advice doesn’t stick (even for ourselves).

Most advice is generic, and lacks any context or affordance for the complexities a founder faces. So while a founder will smile and nod along (they know the advice is good, and they don’t want to look stupid), the gap between the advice and actually implementing it is vast.

This is the problem with “Twitter is a university”. I freakin hate that description. The advice you need to successfully build a business is not on Twitter, I promise.

Second, if the advice is any good, it probably impacts a big portion of your business. Like hiring and firing, pivots, fundraising, firing or ignoring customers. So again a founder will smile and nod to the good advice, only to face the challenge of implementation alone. And likely won’t do it, or will put it off until it’s too late or unavoidable.

So what if we could change things and give advice that would stick? We have a few ways we solve for this at Day One.

1. There should be a lot of listening before any telling. I remember my first 1:1 with a Fellow in our most recent cohort. He came in with a laundry list of questions. But I spent our whole first session asking questions myself, trying to really understand what’s going on - not just with the business, but with the people involved, the motivations, the hangups and insecurities. Real stuff that impacts how you build, and it guides how the advice is given and received. I think answering these questions is also helpful for a founder, forcing them to think and spell out their issues, complexities, and have a strong understanding of what’s going on so they can receive advice well.

2. The advice should be iterative as the founder implements it. Very few things in a startup survive contact with the market. This includes all the best laid plans and advice. So just like a startup needs to iterate, so does the advice. In practice, the generic version of the advice probably doesn’t change, but because we now get to roll around in real world complexity and what the founder is facing on the ground, the advice changes to become real. This happens about 3 to 4 weeks into our Fellowship program for almost every founder.

3. And I think the advice should be followed up with actual help - and not just “let me know how I can help”, but week after week, scrubbing in with a founder to actual work through the implementation of any advice. This is so important because what keeps founders from implementing advice often isn’t even complexity. It’s just the fact that doing some things is so dang hard and painful. So helping, or just being there as hard moves are made, is key. It’s the soft side of advice.

I’ve told people from the very beginning I wish I as a founder could have joined Day One. I’m pretty sure we could have avoided a few of this big mistakes if we did.

So the next time you hear good advice - from Twitter, a podcast, a VC, yes you should follow it, but know that you probably need a lot more to really make it stick. So maybe share more context and ask for deeper insights. Or build that relationship for ongoing support.

A performance coach for founders

Founders know that being an entrepreneur is like being a high-performance athlete. Top athletes have whole teams to keep them at their best. Founders need the same thing. Access to coaches, experts, peers, and connections help founders make the best decisions and shortcut the time to finding customers, pitching investors and shipping product.

That’s why we run the Day One Fellowship - this 3-month program is designed to give founders the support, guidance, and connections they need. You can apply now for our next cohort starting late June.

Are you a fit for the Day One Fellowship? If you’re ready to level up as a founder, let’s find out. Apply here, and we’ll be in touch to schedule an interview if you’re a good fit.