Carrot Exit

After 10 years of working at Carrot (carrot.com), I’ve decided it’s time to move on.

My intention in writing this is to reflect on the amazing run I had at Carrot and look back on my thoughts and feelings during this time.

As I exited the company the biggest things that stood out to me are…

1. Wow – I didn’t think we would make it this far
2. I am grateful for the people and the impact we made
3. SaaS is a great business model and hard at times – but worth it
4. Leading people is easy if you lead with core values and have a CEO with a clear vision
5. Innovation is hard, expensive, and complicated – but 100% necessary for growth

Here are some deeper reflections 👇

Backstory

I attended Oregon Institute of Technology from 2009 – 2013. While there I had a roommate named Justin Parnell. During my senior year, he mentioned an entrepreneur his brother went to school with who was starting a software company. I reached out and was Carrot’s first intern.

In 2012, Carrot was called REITheme.com and sold WordPress templates to real estate investors.

As an intern, I worked with the CEO (Trevor Mauch) making demo videos, working on the website, and learning more about the product and industry.

I left the summer internship and worked in sales for cleanway.com.

However, I would constantly email Trevor the SEO tests I was doing with my blogs and share ideas with him. Once Carrot had enough revenue to hire someone, I came on full-time as employee #4.

Early Days 2014 – 2017

Back in 2014, Carrot was around $20k – $25k in monthly recurring revenue. Trevor and Chris (co-founders) had done a great job finding product market fit.

At the time our main acquisition channels were

1. Affiliates – Trevor had a strong network in the industry and partners were happy to promote for a generous 25% lifetime commission incentive
2. SEO – Trevor and I would write a long-form piece of content each week
3. Webinars – either to our list or with partners to build our email list.

The early days were fun, chaotic, and fast. We would show up on a Monday call and everyone would share their priorities and then get to work.

We all shared live chat and sales call responsibilities. A couple hours each day we would log in to our help desk and voicemail system to handle customer and prospect needs. This is a GREAT way for everyone in the business to be on the same page.

As the team grew we started placing people in more dedicated seats. Our first hires looked like this

1. Jen – Trevor’s EA (Trevor was running multiple businesses)
2. Jake – dedicated chat and email support
3. Alex – all things marketing
4. Andre – support
5. Pete – sales
6. Shaun – product

Marketing during this time was easy. I think it was partially the right place, and right time. We had just come out of a tough real estate cycle (2008 – 2012) and markets were starting to recover.

In addition, many people were realizing they needed a website to generate leads and Carrot was ranking for popular search terms, all over podcasts, and bigger pockets forum posts. It was easy to set big goals and hit targets. I dug up an old scorecard we used to track our marketing.

By this time my role at Carrot was starting to change. It went from…

• Writing blog posts
• Creating landing pages
• Helping Trevor market and close webinars

To

• Running the company roadmap of all projects
• Working with the team on reporting metrics
• Working with sales on things like events, partnerships, etc.
• Building out email automation and funnels
• Starting our Facebook ad campaign

I loved it. Every month there was a new challenge and I was starting to develop into a full-stack marketer. In my spare time, I was creating WordPress blogs and trying affiliate marketing, content marketing and even creating a couple of digital marketing courses. I would regularly rank blog posts right below Carrot for some of our most competitive keywords.

The Carrot Product

This part of the Carrot journey was fun and exciting. We launched so many amazing features that thousands of Carrot members still use today

1. CarrotCast – our podcast which we eventually grew to 20k+ downloads and over 500 episodes
2. Launched our Advanced Marketer plan
3. Keyword tracking – which was a big feature at the time
4. Stats v2 – better analytics dashboard
5. Lead manager – track leads and move them through a simple kanban style board
6. Upgraded our hosting – this allowed for Carrot sites to be WAY faster than the competition. I remember our engineers staying up overnight to handle the migration
7. AgentCarrot – we launched our website product into the Agent industry

Looking back – it was crazy, busy, and a ton of fun.

We did all of this with a team of 8 and some contractors. By the end of 2017, we were well over $4mm in ARR and producing a healthy profit margin.

It was time to scale this thing and see what we could accomplish. We decided to invest heavily in the company in two main areas

1. People
2. Product

Growth Pains 2018 – 2022

As the company grew, we hired more employees and started to focus on things like leadership training, process documentation, and team training.

We realized that 3 of us (Trevor, Chris, and Alex) were slowing the team down by being involved in every project, decision, and meeting.

So we started to build a leadership team and give our flat org some direct reports. Because this was all our first attempt we did the smart thing which was to join masterminds and hire coaches to help us.

Here we are with some of our new leadership team at an offsite

It was also around this time that my role shifted from marketing 👉 operations. I actually remember the exact moment when this happened.

Trevor was a member of Russell Brunson’s Inner Circle mastermind. A couple times of year we would fly to Boise Idaho and be in a room with internet marketing legends like Alex Hormozi, Alex Charfen, and Brandon Poulin from Lady Boss.

It was at one of those masterminds that I pulled Trevor aside and said to reach scale with a marketing team I think you need to bring a more experienced marketer on and let me focus on the day-to-day of the business. He asked what that would look like and I shared my plan to transform the company in several ways

1. Getting our process documentation in order and employees trained
2. Getting the company roadmap and goals following a proven process (OKRs, EOS, etc).
3. Working with our finance team on better reporting and insights into strategic opportunities for the business

I jumped head-first into operations and started doing great work. We also applied for masterminds with Dan Martell (SaaS Academy) and Cameron Herold (COO Alliance).

We learned so much from these groups and made connections that helped us unlock millions in revenue.

But it wasn’t all rainbows and unicorns.

Of course, we went through the challenges of COVID-19 like every other business. We saw exceptional growth during this time…but it also presented some challenges

In hindsight, COVID-19 pulled a bunch of growth and revenue forward. Everyone was at home, most without a job, trying to figure out how to make money. Real estate was absolutely RIPPING and Carrot was exploding with growth from people signing up.

Because we aggressively hired – I was now running, CX, professional services, and the operations team. This was a season of meetings, spreadsheets, and projects.

As we grew we were pressure-testing our newly formed processes and they were breaking left and right.

• I remember project planning docs took forever to fill out, review, and approve.
• We built our first product team and it was hard to get them on the same page as the founders after 5-6 years of just knowing what to do
• We built features our members didn’t ask for or need
• Our marketing started to shift and we lost a bit of our edge
• We focused more on output vs outcomes because we had all these people working for us and they needed to be busy

In short, we grew quickly and didn’t have the right process and people lined up to fully capitalize on that growth. This was a great learning lesson for me.

Some of my favorite accomplishments around this time were

Building the operations team

This team is STACKED with A players.

• Danni – the operations manager is one of the most organized and accountable people I’ve ever worked with. Carrot would struggle without her.
• Jonathan – this guy is a beast when it comes to finances, modeling, and mixing business with spreadsheets. I owe a lot of my success during this time to him. He was a great teammate and an even better person.
• Haley – I first hired Haley as my executive assistant. My stress level went from a 10 to a 5 with her. She is a rockstar with helping keep people organized and focused. She transitioned her role to working with Danni on the operations team and she is the Robin to a Batman (in a great way). She is always helpful and drives projects forward.

Hiring

Before 2018 we would MAYBE hire one person per year. Trevor typically did it and we had some success. The problem was – that the CEO couldn’t be the only one hiring for a growing company. I tapped into the COO alliance and brought back the Who hiring method. Danni was a HUGE part of this process and I can’t remember the exact number but we hired something like 20 people in 1 year.

Were all of them slam dunks – no. But we could move quickly and find talent when we needed it. What took months we figured out how to make work in weeks.

Financial Documents & Scorecards

With Jonathan’s help, we improve our financial documentation and reporting 10x. Leaders had departmental finances of their team, we handled our sales tax liability (no small feat), and had a scorecard that was WAY more accurate and useable. This was a multi-month project and unlocked a ton of insights for the business.

Catching Our Second Wind 2023+

During this time we experienced some turnover on the team. An interesting dynamic started with team members who had been here for 5+ years. They had a perspective and understanding of the industry and the business that newer employees didn’t have.

There were pros and cons to this. Newer employees had different ideas perspectives, and thinking that helped us.

But they also didn’t have some context which forced us to dive back into training and process.

I had another tough conversation with Trevor and Chris about my role. I wasn’t quite COO material and that is ultimately what the company needed.

We couldn’t use our normal hiring process for finding the level of talent we needed so we tried our first attempt at recruiting. Trevor created a list of companies he would love to have an operator from.

I fired up LinkedIn and my copywriting skills and was surprised with my hit rate. I was able to get phone conversations with almost everyone we were interested in.

Enter Angie as Carrot’s new COO.

We hired Angie and it was a night and day difference. She is an incredible leader and person. I loved working with Angie and think she is the perfect fit for helping Carrot grow beyond this next phase.

2023 – 2024 – Big Challenges Ahead

During a leadership off-site, we were discussing the biggest challenges in the business. At the time our marketing numbers weren’t at the level we expected or wanted them to be. Nearly every channel was seeing some sort of decline.

There wasn’t an obvious answer as to why there was such a distinct decline. But we knew someone needed to figure it out. Angie was getting up to speed and making an impact. I had a new role as VP of Strategy but was struggling to make the impact I wanted.

So again, hard convos were had and I stepped in to lead the Marketing & Sales team. I took the role with the understanding that my main objective was to get marketing back on track.

After 9 months of grinding and working as hard as I could – I am grateful for the opportunity but wasn’t able to move the needle.

Perhaps I will write another detailed post on what we tried, what I learned, and some metrics. But for now, I will leave it at – I tried, but it didn’t work.

Before leaving for my first hunting trip of the 2024 season I talked with Trevor and Angie and let them know that I was ready to move on and allow Carrot to bring in an A+ marketer to help right the ship and get growth back on track.

So with that – we made an exit plan, discussed the details, and set a timeline for me to leave the company.

I look back on the last 2-3 months of Carrot and wish I could have figured it out – and I am sure I will. But also equally excited about the future, what is ahead for me, and my next opportunity.

Some Of My Favorite Mishaps While At Carrot

I have so many. None of them were funny at the time, but hilarious to think back on now.

Updating our entire multisite network of sites – on my first day

We all meet in Carrot HQ in Roseburg Oregon for my first day. We flip up our laptops and Chris Carr (CTO of Carrot) is giving me access to all things Carrot. I logged in to WordPress and noticed we need to upgrade to the newest version. Easy, I do this all the time on my websites.

What I didn’t realize was I was an admin and that would update WordPress on ALL Carrot websites. This would break code and cause unknown harm to the hundreds of sites on the network. Sorry Chris. He spent the rest of the AM rolling back the change.

Merchant Account To Test Mode

I still can’t believe I did this. We had a specific product called a quick start. Essentially we would get your website online and dial it in a bit. I was messing around with order forms and testing something new. I moved our merchant account to test mode and forgot to set it back to live – FOR 3 MONTHS.

So imagine my horror when reviewing our P&L and seeing that product drop off a cliff. I finally figured out what was wrong and personally emailed dozens of clients asking if we could charge them 3 months after the fact.

Of the $30k I cost the company I was able to charge $28k of it and reclaim it. I was terrified I was going to get fired after this screw-up – but nope. Trevor appreciated me finding the issue and having a plan to solve it when I told him about it.

Last Minute Webinars

When Trevor and I were doing weekly webinars we would always be testing SOMETHING. I remember there was one particular webinar where Trevor was live on the call. We had something like 200 people watching and he was in Slack asking me to make changes to the order form. He wanted to pitch a NEW OFFER.

I was sweating behind the scenes to make all the changes, test them and make sure we could collect the money.

It all worked out and we made the webinar successful. I remember cracking a couple cold ones after that.

Random Other Mishaps

If you are an email marketer it’s impossible not to send the wrong email or subject line. I remember I once thought I was testing an email and at the last minute I typed in

“How do you like Carrot so far” and hit send.

Well, it went to EVERY single Carrot customer and lead. The cool result though, we got a bunch of responses.

I also remember sending out a survey and forgetting to capture who it was from. This isn’t uncommon except we were going to use the survey to target conversations with specific people – so that was a waste.

Plenty of other things like deleting things that we could never recover and all other sorts of moving fast and breaking things – but lessons were learned.

Conclusion

I am grateful for my time at Carrot. I’ve shared a lot of the reasons why above. I learned a lot and will take those lessons for the rest of my career.

But I felt burned out towards the end. I needed a big shift in my workday to get back to creating vs managing.

Here is what I am currently working towards…

1. Becoming a better writer (copywriting and general idea sharing)
2. I want to grow my personal audience on platforms like Twitter and LinkedIn
3. I want to build a SaaS product and market it with everything I’ve learned
4. I want to grow a couple blogs I’ve been tinkering on for years
5. I want to work out consistently and be the best husband and father I can

I am open to joining another team shortly – but for now, I want to work on my skills, keep my stress low, and deeply think about what is next for me.

If you made it this far – good for you, there is a lot of text above.

Reach out if you have an opportunity you’d like to explore with me.