Six Months In...

Six Months In...

This week marks month six since I left my full-time role as a Product Manager and went full-time on my start-up, Xoba. While I was expecting a rollercoaster, I didn’t expect it to be this wild of a ride.

After taking time to reflect this weekend, I wanted to share some of my thoughts, experiences, and learnings thus far.

My Wife is Amazing

Well, I already knew my wife is amazing… hence why I married her. I can write an entire blog post about how amazing my wife has been, especially over the last six months, but I’ll keep this one short. She’s been my rock throughout all of this. She has been so patient, helpful, and understanding, and I couldn't have made it the past six months without her. So a word of advice for everyone trying to start something, have a rock. That rock could be a significant other, a best friend, a sibling, or anyone. But you need someone to listen to you and bring you up when you’re down.

Leading Friends Is… Weird

One of the hardest challenges thus far has been working with my friends. The people I'm trying to build this company with just happen to be people I’ve known. Going from being friends and peers to then having me in the CEO role was a challenge for me. Since they’re friends, I wanted everyone to like me and I wanted it to feel like I wasn’t just pushing my own agenda. We were wandering in different directions for the first few months, and we struggled massively because of that.

It took time for me to realize that everyone was looking at me to set a company strategy and hold everyone accountable. Once I realized that, I set up more 1:1s and departmental meetings focused on learning and taking input from across the team. Then, I took the input, crafted a strategy, and presented it to the company. It was a game changer for us. When I first did that, it felt like a weight was lifted off my shoulders, and I felt much more comfortable as a leader moving forward. We had mutual respect for one another as friends and colleagues, but I needed to be the lead and hold everyone accountable.

Filter Advice

What I didn’t realize was that everyone wants to give you advice. I had countless people reach out to me expressing interest in what we were working on and offering to hop on calls and give advice. Our discussions would range from the logo to marketing strategy to product strategy to swag. It was a great feeling for the first couple of months until I realized it was actually causing more problems than what it was worth. I ended up second guessing myself countless times, gave conflicting direction to the team, and simply just wasted too much time.

I was always receiving conflicting advice. One day one person would tell me I should be doing X. It seemed logical and it wasn’t an area I knew a ton about, so I took their word for it. I’d sync with the team the following morning and suggest we take his or her approach. Then, later in the afternoon, I’d speak with another individual who would give conflicting advice and say that what we were doing before was smarter. I would go back to the team at the end of the day and tell them we should switch back to what we were doing before. It caused the team to be confused and frustrated, and frankly, me too.

It took me a little time, but I realized that I should be the one going out and seeking advice, not the other way around. When I would go to seek advice, I had specific topics that I needed help with and could find the right person (or the couple of people) to speak with regarding these topics. Then, I could compare my notes against everyone’s thoughts and make a more informed decision. Once I made that switch, I’ve been happier, and the team has been more satisfied and more productive.

Something is Better than Nothing

My motto has become something is better than nothing. I found the team stressing over every detail of a message or a feature, and we’d paralyze ourselves and take too long to ship something. We didn’t want to put junk into the world, but once we put something out there, we got people talking, received feedback, and were able to iterate quickly. So I told the team ‘let’s get something out there, and if it doesn’t work, or needs refinement, then we’ll take it from there’.

My favorite thing to do as a PM was to come up with a few variants of a feature that I thought would make for decent solutions after doing some initial research and hypothesis testing. Instead of listening to my customers ramble for 45 minutes about the 500 things they needed, I was able to extract concrete feedback within 5-10 minutes with just a basic mock-up. Something was and still is better than nothing...

Start with your Goals and Objectives

In the beginning, my co-founders and I put together a six-month plan that outlined the focus for each month and the milestones we wanted to hit. We knew it was going to change, but at least we had something down on paper we could strive towards and check ourselves against. The problem was that we were getting conflicting advice and I struggled in the beginning leading my friends and holding them accountable. So, for the first two or three months, we ignored the plan and just ‘went with it’.

For that time period, we went in circles. We seemed to be changing strategy weekly and the team didn’t have a sense of direction. The team was confused and didn’t know exactly what we were working towards and how we know when we’ve actually accomplished anything.

I remember going to the park with a notebook in hand and just spent the morning writing down all my thoughts. During that time, I knew that we needed to implement some kind of framework to set goals across the organization and a way to hold ourselves accountable to those goals. So, the following week, I drafted a new strategy. I made it clear what we were working on, what we weren’t working on, what our core objectives were, what we were going to do in order to work towards the objectives, and how we were going to measure ourselves. The goals and the strategy you set out might be the wrong ones, but going back to my motto of ‘Something is better than nothing’... it gave our team a way to align on something and have a sense of where we need to go.

Now, on the first of every month at our all-hands, we reflect back on the previous month. What went well? What didn’t go so well? Where should we be doubling down on? Then, we review the current month’s strategy and goals. At the end of the all-hands, everyone is clear on the plan, who owns which parts, and the expectations. At every all-hands throughout the month, we spend the first 20 minutes reviewing the plan, tracking our progress, and course-correct if needed.

We also now take it a step further and craft daily and weekly goals. Every morning our team gets together in a brief standup for 15 minutes and we go over what we accomplished yesterday, what we didn’t, and what we want to accomplish today. It’s a great way to keep everyone aligned across the team and aligned to our larger goals and objectives. It’s the best 15 minutes of my day.

Over the past three months, this approach has been one of the most beneficial things we’ve done as a company.

Data Data Data

One area I was most excited about when starting a company was my ability to build out a data pipeline and to play around with data. Data was an area of frustration for me at my last organization, so I wanted to change that with Xoba. My advice -- From the get-go, build a plan to collect and analyze data across your organization, from marketing to user data. Even if you don’t think you’ll use it for a while, it’s better to start collecting it from the beginning.

Having some level of data is a way to start a conversation, test hypothesis, and track goals. Going back to our monthly plan, we always have a baseline, and that comes from the underlying data we collect and present.  Whenever we release a new feature, we have a section in our PRD called ‘Analytics’. So our engineering team knows when building a feature what we’re aiming to measure and can implement it from the beginning.

I recall one of our advisors asking, ‘Hey, how many of your users are doing X then Y?’. That pattern never occurred to me, but since we had been collecting data from the beginning, I could extract that data pretty quickly, and I learned something fascinating about our usage patterns. Then, our minds started to race and we sliced and diced the data in different ways, uncovering more about our users, the marketing approach, and more.

My advice is to have three core KPIs that you believe are important to your business, track them, and report on them frequently. These KPIs will change as your business develops. For example, one of your core KPIs the first six months of your business might be the number of newsletter sign-ups, but then at six months, it might be newsletter to user sign-up rate. Align your KPIs to your goals and objectives, measure them, report on them, and talk about them. If the numbers are bad, bring them up to the team and focus on how you can improve them.


Six months. I’ve never second-guessed myself more, had more lows, doubts, and struggles in the last six months than probably in my entire life. But, I’ve also learned so much, have had the opportunity to meet so many amazing people, become a better leader, and have higher highs than ever before. This whole startup can crash and burn tomorrow, but I wouldn’t trade this experience for anything else. It’s genuinely something that you need to do yourself to truly understand what is going through a founder’s head, the challenges they face, and the mental stamina they have or have developed.

I’ll continue to dive into specific topics around being a leader at an early-stage startup. Subscribe below to keep up to date!

Show Comments