Reflections on the first 90 days of building Freshpaint

As 2019 comes to a close, I wanted to take some time to reflect and document what building Freshpaint has been like. Coincidentally it’s also been a little over 90 days, so this post basically doubles as a ‘first 90 days’ reflection as well.

We decided near the end of YC (we’re part of the Summer 19 batch) to pivot from Perfalytics – the Postgres performance product my co-founder, Malis, was originally working on solo – to Freshpaint. It was at this point that I joined the company full time as a co-founder (I had previously been helping him on the side, which I encourage anyone that works in tech to do with their friends – you never know what projects will catch fire or which relationships will flourish).

For context, Freshpaint automatically collects data from your site or app, and in one click sends it to 100+ analytics, product, and marketing tools. We make it dead simple to integrate tools, standardize and govern data across your stack of tools by collecting data once, and save developer resources to focus more on product.

Some of this list might feel “well yeah, duh dude”, but startups are so complicated that it’s easy to just miss the basics sometimes. A few things that stand out to me right now:

1. It’s hard AF

This is the first thing I tell anyone that asks me some form of “how is it being a founder?” or “how’s the new startup doing?”: It’s hard AF.

The very next thing out of my mouth is that it’s the most fun job I’ve ever had.

It’s likely those two things are related: the most challenging job I’ve ever had is also the most fun job I’ve ever had.

But yeah, it’s super hard. Of course I knew it was hard going in, but I wasn’t prepared for the kind of hard it would be. I thought it was going to be something that was difficult, but could be mastered with enough input – sort of like taking a really hard test.

Instead, it’s a different kind of hard. It’s like going through a really bad breakup – one that just keeps going and you have to just find some way to manage. The minute I master something hard AF with Freshpaint, a new thing evolves that’s also hard AF – it’s a continuous cycle that I’m prepared will never go away. This equates to a constant evolution of skills, which is the interesting fun edge of the double-edged sword.‍

2. Focus and prioritization are the most important

The biggest adjustment for me as a first-time founder was this: if I don’t do it, it likely doesn’t get done.

Here’s a very real example: We invoiced a few customers and a few weeks later we were sent a check by one of them. I open the Silicon Valley Bank app to deposit the check and couldn’t. Four phone calls and three hours later, I figured out what was needed: I needed to sign something and SVB needed to check a box on their end.

I left that day finishing exactly none of the things I had planned to get done.

And things like this happen every. single. day. 

It’s so easy to spend an entire week doing lots of things, feeling busy, but not actually moving the business forward. It’s so easy to get your lawyers, get your business cards, and “play” company as opposed to focusing on the tasks that progress the business forward in a meaningful way.

Even while employed at larger companies, I never once used business cards.

3. It’s way easier with a co-founder

This is for a few reasons. Practically speaking, it just gives you more bandwidth to get stuff done. In the early days of a company raw hours put in are meaningful. If your average founder works 60 hours each week, then 2 founders can get 120 hours of work done in that same time period. Of course you don’t get exactly 2X output, just like when a team at a larger company goes from 4 to 8 – time gets sucked up updating, communicating, coordinating, etc. But the impact of 2x in bandwidth on an early stage startup is real. One of us can focus on product and tech, and the other can focus on selling and customer development. And when we start raising money, the business doesn’t have to be put on pause: one of us can focus on fundraising while the other can continue to operate like business as usual.

The other reason is a little more personally applicable. I’ve learned this about myself: I tend to be externally motivated. This means that I’m more productive in an office than working at home, projects progress faster when there’s another party involved than just myself, and even something as simple as telling someone about my goal pushes me more than I would myself. My co-founder keeps me accountable whether he means to or not, and I have the same affect on him. 

Here’s the thing about co-founders: you need to trust each other. In the early days of a startup there’s a billion different micro decisions that are made every single day. If you worked to consensus on each one, you’d literally never get anything done. We trust each other to correctly make small and medium decisions without input from the other party. We trust each other’s judgement to identify bigger topics that do need to be discussed, and to actively raise those. And we verbally affirm this trust with each other: there’s countless times each day where we tell each other “Whatever you decide for X, I trust you”. If you don’t trust each other, you’re screwed.

We also celebrate the small wins together. Inbound by some supposedly prestigious VC firm. Feedback from customers “this is exactly what I was looking for”. The “Wow that’s actually really cool” reaction when we tell people what Freshpaint does. 
‍

4. You have to put in the work

Once your startup enters any GTM phase (customer development, sales, etc) it can be pretty surprising how much work you have to put in to get your first customers (or customer number 1,000). Of course some get lucky and have plenty of inbound demand on Day 0, but for most SaaS startups out there that’s likely not the case. Even if you’ve built something people want and actually solves a real burning problem, you’re probably in a place where nobody knows you exist! 

It’s not uncommon for me to meet other YC founders at this stage (just getting GTM off the ground) who are sending upwards of 100 high-quality, targeted outbound emails each day. To be clear, spamming people is not the best way to get your startup off the ground. If you’re outbounding, you have to send relevant, super-high-quality emails. Each of these is custom, and often takes many minutes to write. So there are many days where I will sit there for 7 hours straight just sending outbound emails.

The company isn’t going to magically build itself. If you don’t do the work, it just doesn’t happen.

5. Your reasons for starting need to be the right reasons

Sure we want to make some money. Sure we want to build something that solves a problem. Sure we want to create something that’s used by a ton of people.

But when things get tough, it’s easy to think “why the heck am I doing this right now?” Because all those things above (money, scale, solving real problems) you can get at Google, Facebook, or any other company without the headache and heartache.

When I was thinking seriously about starting a startup, I talked to about 25 other founders on their experience, things to look out for, tips, tricks, and shortcuts. To save you the trouble: there’s no shortcuts.

But one person I spoke to in particular pushed me to take a different angle with my decisioning. He told me to focus on my why and think of what I want my legacy to be. He told me to flip the script for a minute and don’t look at all the opportunity in front of you (money! problems to solve! fame! yachts!) because it’s too easy to get fired up about that stuff. So I started to look at it from the perspective of "your company is definitely going to fail in 2 years, so what do you want to have gained from that journey?"

And that shift in perspective gave me a ton of clarity (thanks Sam!). I ultimately decided that I wanted to have the life experience of starting a tech company. That was it: that’s the thing. Ultimately I think Freshpaint will exist whether we’re the ones to build it or not. Even if we fail, we don’t make any money off of Freshpaint, nobody wants our product, and we solve zero problems in the world I’ll have the experience of pushing myself and my cofounder to get something off the ground and grow it.

And when things get super difficult, I try to remind myself “This is what you wanted. This moment is exactly what you wanted when you were thinking of starting this company. The reason you started this company is to feel exactly this thing in this moment, and then choose to keep going.”
‍

6. Stress will eat you alive, but only if you let it

Doing a startup is kind of like racing a marathon. Yes, of course it’s going to hurt.

And you know it’s going to hurt before you start doing it. So don’t be surprised when you’re in the middle of it and it totally sucks. Just settle in and be ready to work through the pain.

(To be fair, I’ve never actually run a marathon. But I was a competitive D1 distance runner and have put in my fair share big races and 100 mile training weeks, so I feel like I have some credibility with this analogy.)

There’s a baseline level of stress that is just a constant hum in the background, and you can actually get quite comfortable with this. But when things with Freshpaint get particularly stressful and go above that baseline, I’m not surprised. It’s what I signed up for.

The solution for me is balance, only now I have to actively fight for balance. It’s too easy to come home, open up my Macbook and just keep working. I now have to forcibly make time to exercise, to read something other than startup/business books, and spend time with my partner.

It might be counter-intuitive, but that time away from Freshpaint is actually additive to my company. When I’m on runs alone, skiing, reading something totally unrelated to work, or cooking something elaborate I often have my best ideas or thoughts on the business. The key is to have a notebook or iPhone close so I can make a note.

7. Prioritize sleep

Honestly if you don’t do this, you’re doing yourself and everyone around you a massive disservice. It’s idiotic to not prioritize and invest in sleep.

I am a late-night person so I often struggle with two things:

• Going to bed at a reasonable hour.
• Waking up before 8am.
  

Some tactical things that have helped me sleep better and you should definitely try:

• No sugar in the morning. Sugar is super bad for you. It’s especially bad in the mornings: your body gets the sugar rush, and a few hours later the resulting sugar crash. As a result, your body craves sugar. Once you start the sugar high, you need to keep feeding it to avoid the crash. My breakfast these days is typically water and oatmeal with some cinnamon.
• No caffeine. It totally screws with your circadian rhythm. Caffeine has a pretty long half life at 6 hours: which means that if you drink coffee at 2pm, at 8pm there’s still half the caffeine in your bloodstream.
• Try to exercise regularly. I always sleep better when I exercise.
• We changed all of our light bulbs in our apartment to soft white. This removes some blue light from our living environment, and makes the house just feel better.
• Flux. Just get it.
• Dark mode: Turn on dark mode for all apps, dark theme for gmail, and get the dark reader chrome extension (turns everything into dark mode!)
• No screens at least 1 hour before bed (I’m still not great at this). I try to read a book.

8. Everything is a funnel

When we started working to get our first users, we began where most startups do: by reaching out to a bunch of people with varying degrees of warm and cold outreach.

At first my outreach sucked. As in I send hundreds of cold emails and got zero conversions. We were able to get meetings with people in our network, but in terms of cold outreach my efforts were not converting.

After some work, we’ve since solved that problem. But now we have a new problem – we’re booking meetings (yay!) but we’d like to have more of the people we talk to install Freshpaint.

And I’m sure once we solve that, the next problem is how to convert more of those new users into paying customers.

And after that: how to get them to renew and expand their contracts.

This is just one example, but more and more I’m seeing that the funnel mindset can be applied to almost any area of the business. It’s a simple mental model that helps you break a problem down to its fundamental parts, focus on the part that’s broken right now, and disregard the parts that don’t matter yet.

9. Get mad at the world and keep a list

• Setting up payroll? Still takes a few hours with Gusto.
• Want to deposit a check? I spent 4 hours getting us the ability to deposit a check with SVB a few weeks ago.
• Okay now you want to send a wire? Print these 3 forms, sign them, scan them back to us, wait, and then call 3 times to follow up. Seriously.
• Need a credit card for the business? Brex is making it easier, but the rewards program is meh. Getting approved for an Amex is hard if you’re 22 with a thin credit file (lots of YC founders fit this profile). I’m an anomaly because I have done more adult-y finance things like bought an investment property, got a bunch of credit cards because of the points, chained myself to the guillotine of student loans, etc.
• Want to implement some popular library into your product? Here are 4 different things about it that feel way harder than they need to be.
  

The list goes on. We loosely keep a running list of all the crap we have to deal with that is fundamentally broken. I allow myself to get frustrated and mad, so I can truly feel the pain. If you’re curious, PG has a great essay on this and Ryan Petersen (Flexport Founder/CEO) frequently talks about this as well.

We constantly find ourselves talking about these challenges. At the end of the day we’ll sometimes share with each other how surprisingly tricky some random thing was, and the way we know how to make it better. Then we say “well if we ever need to pivot again we can look at that”.

I actually think Freshpaint falls into this category for a lot of founders and teams at larger companies. The legacy way of collecting data is very manual and usually requires someone with technical expertise like a software engineer. This is painful for all involved. It’s painful for the analytics or marketing professional who needs the data in their tools, and it’s painful for the software engineer because it distracts her from her actual job building product.

And if you have 5 different tools in your stack, you have to go through that process 5 different times.

You should be able to get these tools up and running with the right data in them in just a few clicks. Getting the right tracking in place shouldn’t be as tricky as it actually is for many. Software engineers, often a company’s more valuable workers, shouldn’t have to deal with the distraction. The marketers, analytics, and product managers that use the tools shouldn’t have to tap an engineer on shoulder and beg them to fit it into the next sprint.‍

10. Lawyers are expensive

Freshpaint as a company has existed for about 8 seconds, and we’ve already spent $17,738.70 on lawyers doing lawyer-y stuff. What surprised us was how quickly legal fees can balloon. To be clear, there is no other category that Freshpaint as a business as spent more money on in 2019 (not even office space in SF or payroll!).

We’ve used that $17k-ish for initial corporation, some intellectual property stuff, and I joined later as co-founder so we added me and changed the stock plan around a bit. It’s also important to note that our business exists in a space where data rights and privacy of our customers’ users has to be carefully taken into consideration and looked after, thus we need to understand and be compliant with both US and international laws.

Maybe that’s too much and we’re doing something wrong (is it? please hit me up on twitter if it is). I feel like it's normal stuff, but everything is $800 here, $1,500 there, and it just adds up. Whatever the case, kudos to the capitalist lawyers who figured out how to get $20k in revenue from a 2 person company that’s less than a year old and has like no revenue. I wish to emulate your vSMB (very small/medium business) revenue strategy one day.

Onward and upward!

I’d love your thoughts on all of the above. We’ll be writing more about our journey building Freshpaint, Y Combinator, and things we learn along the way.

If you think Freshpaint sounds interesting and you’d like to learn more, you can get started for free here.