Leaving A Corporate Job To Start A $6K/Month Conversion Rate Optimization Company

Published: July 24th, 2020
Jacob Dazzeo
Founder, Watson Digital
Watson Digital
from Portland, Oregon, USA
started June 2019
Discover what tools Jacob recommends to grow your business!
Discover what books Jacob recommends to grow your business!
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Hello! Who are you and what business did you start?

Hello Starter Story readers! My name is Jacob Dazzeo and I founded Watson Digital. We are an innovative online marketing company that focuses on three main products to help businesses grow their online sales funnel.

Our core products are Conversion Rate Optimization (CRO), Pay-Per-Click Advertising (PPC), and Social Media Remarketing (SMM). In less than one year I was able to completely replace my corporate salary while cutting my work week down to mirror the Tim Ferris’ 4-hour workweek.


What's your backstory and how did you come up with the idea?

My first job out of college was an internship with the Portland Trailblazers. The internship was amazing but a future in ticket sales wasn’t what I was looking for, so after the season, I decided to look for a job in a growth industry. I took an entry-level sales position with a rapidly growing (and eventually award-winning) digital marketing company.

You’ll go further with help. Watson Digital is what it is today because of support from friends and family. We are always looking to form strategic partnerships that benefit both sides.

Taking the company’s proven sales method and adding my own creativity helped me rise to Sales Manager in just 2 years and put me on track to start my own department or become a General Manager.

While pushing towards my sales goals, I was also taking the initiative to learn from the company’s best minds in PPC, SMM, Search Engine Optimization (SEO), web design, and more. I would spend hours of my own time and take advantage of company approved time to watch, learn, and question the methods used by these experts.

With growth, the company I worked for started to implement and enforce policies that discouraged the creativity that had led me to many internal sales awards. Although I was on track for upper management positions, I decided to take my knowledge and relevant experience and branch out on my own.

To be honest, I’ve never enjoyed working for someone else so I had been looking for the opportunity to be my own boss since high school graduation. I started 3 businesses before Watson Digital and either lost money or broke even on all 3. Starting Watson Digital was a risk that I knew I needed to take for my own wellbeing.

Take us through the process of designing, prototyping, and manufacturing your first product.

Our initial service offerings were very similar to the service offerings of the company I had left to start Watson Digital. I had a lot of expertise and knowledge in multiple digital marketing disciplines but limited hands-on experience so I offered everything I knew I could do.

The first version of our website offered PPC, SMM, SEO, and website maintenance. After working on projects in each category, I began to realize how we could best assist companies and that realization is what led us to our current product offering.

Describe the process of launching the business.

Since I had freelanced for a bit before becoming an LLC I had a couple of clients which made it possible to sustain until my sales process bore fruit. I built the first version of our website by hand having never built a website before. Everything was bootstrapped and I was literally working on a desktop computer in my bedroom. My only startup expenses were $200 spent on hosting and registering my LLC.

Fortunately for me, when I had attempted (and failed) to sell my previous business, I had met Sergio Fernandez in the Small Business Owners United group on Facebook. The relationship I had begun to build with him is a huge reason for my success today. With his help, I was able to pick up a few clients from the SBOU group and we started to work on projects together. We’ve since worked on over 10 projects together and his company built our new website...but more on that later.

The biggest lesson I learned early is that the best way to grow is to grow in a controlled manner and to create mutually beneficial relationships early on. By growing in a controlled manner, I’ve avoided many of the pitfalls I saw when working for other people. By creating mutually beneficial relationships, I have been able to grow faster than if I was on my own.


Since launch, what has worked to attract and retain customers?

We’ve been fortunate to have amazing clients who have helped us grow through referrals and by entrusting us with additional pieces of their online strategy.

The crazy thing is, we’ve grown without putting a single dollar into advertising so far. We’ve used GMass to send out batches of targeted cold emails for free and scoured freelancer websites for companies already looking for help.

Our biggest win was our partnership with Sergio at Buena Vista Social because the SBOU group has brought us so many great projects and his team at BVS provides complementary services to ours. Our partnership with BVS allows us to assist our clients with just about any need they have for their business which means that they grow with us and become more embedded with our company.

Client retention has been our biggest focus. We’ve lost less than 1% of our clients since we began. The key to client retention for us is building a strong relationship with our clients. We put a priority on communication and transparency which resonates with our clients and differentiates from most other agencies. On top of that, we set realistic expectations which makes it easier to deliver 99% of the time and over deliver often.

How are you doing today and what does the future look like?

Like I said in the opening section, I’ve replaced my corporate salary while shortening my work week. I was also able to bring on my fiancée as a business partner who works with me full-time. She has as much experience and knowledge in the industry as I do plus years of customer service experience. She’s been able to significantly increase the efficiency of managing our client accounts which have improved our client’s ROI. By leaving our corporate jobs we’ve increased our quality of life tenfold. My only nightmares are about rejoining the corporate world.

May 2020 was our biggest month when we brought in over $8,000 in revenue while keeping our monthly expenses under $500. Our steady growth has afforded us the opportunity to invest in our growth moving forward.


With the help of Sergio and Buena Vista Social, we launched a beautiful new site, that hones in on our three core products. We also just hired Ted Adams and his team at Threo to help with our sales process. Our achievable goal is to be a six-figure company by the end of 2020. To achieve that goal I would like to see the $6,167 MPR figure increase to $8,000. Our big dreamer goal is to bring that MPR figure to $15,000 by the end of the year which would require us to bring on some additional staff to ensure we continue providing a high-quality service.

Through starting the business, have you learned anything particularly helpful or advantageous?

You’ll go further with help. Watson Digital is what it is today because of support from friends and family. We have succeeded in having supportive clients who love our service. We have grown with the help of Sergio and his team. We are always looking to form strategic partnerships that benefit both sides.

Figure out what separates you from your competitors early and embrace that. Our clients love that we are more communicative and reliable than other agencies that they’ve worked with. We personalize the relationships we have with our clients which has led to our high retention rate.

Form healthy habits in your personal life. Give yourself time to relax. I exercise, have hobbies, and meditate regularly. I see friends and family often. I eat good food. Just because you started a business does not mean you need to give up your personal time.

Don’t get caught up in comparing your business to others. Stick to your goals and don’t be distracted by the success of others. There are plenty of companies that have grown quicker or are bigger than mine but I’m steadily achieving all of the goals I set out for with my business. Maybe I would be twice my current size now if I had worked more hours or made more sales efforts but money is not the only indicator of a successful life so balance is key.

What platform/tools do you use for your business?

ClickUp - Imagine Trello, Asana, Docs, Sheets, Slack, loom, and more all in one app. That’s ClickUp. It’s the easiest way to manage our projects and incorporate the entire team.

WordPress is our #1 choice for client website projects due to its ease of use and vast customization options.

GMass is a fantastic tool for bulk emailing.

The Small Business Owners United group is great for advice from other entrepreneurs.

Threo has impressed us so far for assistance with sales.

What have been the most influential books, podcasts, or other resources?

Much of our business is communicating with people. That’s why I enjoy the Armchair Expert podcast to keep informed on current events and pick up conversationalist tips.

How to Win Friends & Influence People & The Third Door are the books I recommend to any and all entrepreneurs. I’m heading a book club project in the SBOU group that we hope to launch within a couple of months so check it out for more recommended reads.

Where can we go to learn more?

Start by visiting our new website and take it from there.

If you have any questions or comments, drop a comment below!