Lessons From My First Year as CEO

After listening to Tim Ferriss and Matt Mullenweg talk about long-form writing on Tim's podcast, I was reminded about the joy and clarity of thought writing gives me. As part of my 2024 resolutions, I am going to start writing here more, primarily about my entrepreneurial journey and thoughts on the creator economy.

We'll start this year by reflecting on last year, my first as a venture-backed CEO. In future posts, I'll dive deeper into each point.

Here are the top 10 lessons I learned during my first year at CEO.

1. Start with an Extremely Focused Product

Everyone wants to be an end to end platform or an all-in-one solution. They look at comparable businesses but forget that those businesses are 10 years old (maybe that’s just me). I forgot where I read this, but you have to “earn your way to becoming a platform.” No one starts as a platform on day one.

So start small and think big. Figure out what the ONE thing your product does that’s better than anyone else’s and focus on that pain point. More features won’t make your sales easier. The next feature fallacy is real and I was definitely the reason why Slice fell for this.

2. Make Sure Your Product's Pain Point is Critical

Are you a vitamin or a painkiller? The famous startup question is vital to your early traction. Not all business pain points are crucial. There are plenty of problems that are real, but low on the priority list of potential customers' pain points to solve. Even if your solution is more efficient and cost effective, if the pain point is low priority, selling your solution will be hard.

This was a problem that we had early on. Our first solutions were nice to have but potential customers, even friends of ours, didn’t sign up because the urgency wasn’t there. We are still overcoming this, but we are in a much better situation because we talked to our customers and potential customers to hone in on what was CRITICAL.

3. Messaging Is Underrated but So Important

Unless you’re building the millionth note taking app, chances are you’re building something new. People don’t understand new and you don’t have five minutes with everyone to explain what your product is. Being able to explain your product in two sentences is key to early success. I once had a potential investor tell me, “Jesse, I need to be able to explain this to the investment committee quickly, in terms they understand.” At the time, I didn’t have that two sentence description.

April Dunford has written extensively on the topic of product positioning and I’d highly recommend her book, Obviously Awesome .

The two things that really started me down a clearer path of product positioning were:

A. Realizing I had a problem. No one understood what Slice's product did, including early employees. Sometimes after a product demo, the potential customer was confused. This meant I was confused and not making the value clear. I had to go back to the drawing board.

B. Don't reinvent the wheel. Anchor your description with a known comparable. Some people hate this because it makes your product seem more derivative than innovative, but being able to say “Think Salesforce + Wise” or “Uber for Dog Walkers” helps accelerate the clarity of what you’re building to someone brand new.

I can get much deeper into this, but that's for another post.

4. Map Your Customer Persona, Pain Point, and Product Feature

Early sales for any new business is extremely difficult. Knowing what type of company, who the person in charge is, and what their pain point is will make selling easier. I failed at this so many times in our pre-revenue stage.

I ran into one of these two scenarios nearly every pitch. The C-Level like the product, understood the value, but didn’t personally feel the pain point. The job would get done with or without our product. How painful it was for their team wasn’t their pain point. So our sales cycle became quite difficult. This goes back to lesson 2, is the pain point crucial?

Once we aligned the product, the decision maker, their pain point, and our unique selling proposition, we had a clearer sales cycle.

5. Hiring is F**king Hard

Recruiting talent to your startup is one of the most important things an early stage founder can work on. You can’t do everything and if you don’t have people you can trust, you are finished. Hiring the right people is one of the most difficult and time consuming things I had to do this year.

It would not be an exaggeration if I told you I looked at roughly 10,000 applications and resumes over the past year. I interviewed around 200-300 of those resumes and ended up hiring ten of those candidates full-time.

Even in this tech winter, with layoffs flooding the market with talented individuals, hiring is still incredibly difficult. The reason is simple, think of a 3 circle Venn diagram. In one circle you have qualified candidates, the second circle is candidates within your budget, and the third circle is candidates who want to work with you. The reality is, as an early stage startup, it’s not a Venn diagram at all, it’s really just three separate circles.

My job as CEO is to pull those three circles together as much as possible to find the right candidate. I whole heartedly believe that I was able to do that and while our team is quite lean, I have a LOT of confidence in each of them.

I go by the “Fuck Yes or Fuck No” rule of hiring. If the candidate isn’t a slam dunk, “Fuck Yes!” hire, then it’s a no. There is no in-between. Don’t settle because you feel like you need to fill the position. I’d rather spend a few extra weeks finding the right candidate than redo the entire process in 3 months when the "maybe" candidate flames out.

6. Being Busy Is Not the Same as Productive

This is the number one killer of young companies. People like to feel busy. Being busy is like eating potato chips, they are empty calories. You feel full, but you receive no nutritional value.

At a large company, you can get away with being busy and a little productive. At a startup you cannot. You HAVE to focus on what is productive. What moves the needle.

There are days when I am busy for 12 hours straight, but if I were to do an audit of my time, I didn’t accomplish anything that moved the needle for our business. My time wasn’t spent on sales calls or customer interviews, rather it was spent on financial projections and copywriting. Not that those aren’t needed, but neither of those tasks are what I needed to do to move the business forward immediately.

Focus on productivity.

7. Find an Anchor Customer

I am clearly thinking B2B here, not B2C, but I have seen an anchor customer help many young companies. An anchor customer helps in several different ways. First, it helps solidify early revenue. Any revenue at a young stage will help. It will also help you with case studies. Lots of potential customers don’t want to be the first, but they’re willing to be second. If you can point to a paying customer, others will feel more comfortable signing on.

If I were to do this all over again, I'd work on getting an anchor customer before I even had a product. There are plenty of blog posts on this topic, but it's always better to drive demand before you have a product than try to find demand afterwards.

8. Forget Projections and Scaling Tactics

I spent a lot of time working on projections that spanned anywhere from 12 months to three years in the future. Our investors wanted to see this and they wanted to know how we planned on reaching these numbers. All reasonable and logical. However, every single projection I created was wrong within months.

At early stage startups, pre-product market fit, projections are (almost) a waste of time. You’re putting too much time and energy into numbers that don’t mean anything. You don’t even know how to sell your product to one customer yet, let alone in a repeatable manner. Don't spend too much time on this. Work on getting your first 10 customers who love you.

9. Projections Do Have (some) Value - Know Your Serviceable Obtainable Market

Projections aren’t TOTALLY a waste of time. While I spent way too much time on them over the past year, projections really helped me clarify and understand realistic sales/growth numbers. What was our serviceable obtainable market (SOM) to build a sustainable business?

In the early stages you are split between two realities. One, all your investor conversations are around total addressable market (TAM), hypothetical, large scale numbers that are “pie in the sky” and not in your every day world. Second, you don’t have any customers so you have no idea what it takes to get one sale let alone a repeatable number of sales. In between these two worlds is where your company should end up.

Running an early projection will help you understand what it actually takes to build a $1 billion company and not just blindly say it because your TAM is $100 billion.

10. Trust Yourself and Have Conviction

When I interviewed Pintu CEO, Jeth Soetoyo, on my podcast, he said every entrepreneur needs to find their conviction . Every entrepreneur is going to go through dark days, days where they question everything. So many people are telling you "no," at some point you might start to believe them that this impossible. But you started this company for a reason. You can’t give up because of non-believers. You need to find your conviction to get you through the times where your confidence might be shaken.

Nvidia CEO Jensen Huang was quoted in saying “How hard can it be?” Successful entrepreneurs have to trick themselves into a mental state that will position them for success. Trusting yourself and having conviction will help you get to that mental state.

2024 is going to be a critical year for Slice. By the end of the year we’ll know whether or not we are going to be in business in 2025. This time next year I expect to write a similar post this time next year with a whole host of new lessons.

Follow me for more updates as 2024 unfolds.