February 17, 2022

How To Test Your Way to Massive Scale Ryan Pitylak

This week on the Scale Academy Podcast, Ryan Pitylak, Chief Marketing Officer and Founder of ZenBusiness, joins Ned Arick and Hilmon Sorey to talk about ZenBusiness' initial go-to-market strategy, crucial pivots in strategy, and how they've been able to scale all while helping small business owners live their dream.

Go-to-Market Strategy

Ryan explains that they spent almost a year trying to figure out what their offering would be, exactly who would be the right customer for ZenBusiness, and how they were going to package and position it. In the early days, they were doing a lot of landing page tasks and bringing a lot of value propositions out. A lot of testing went into it. Listen at 00:32 to learn more.

The Inspiration

At the core of the business, Ryan explains that they have always been ultimately trying to figure out a way to help people more successfully start their businesses. It has been a very ambitious goal. The initial interest and ambition came from being around the small business community where they were specifically focused on early-stage companies that were building up products and getting funding. They wanted to figure out how to take their interest in helping entrepreneurs to a much larger scale. Listen at 01:39 ro learn more.

Mapping It Out

Ryan is a believer in the lean startup methodology in the beginning, so, he explains, there was a fair amount of investigation into what was happening in the competitive landscape. They tried many things that they thought were innovative as far as how to onboard people, they used a lot of little tests along the way, a lot of different combinations. And they did all of this before they started to do any scaling. Continue listening at 03:40 to learn more.

Securing the Initial Customers

At 05:40, Ryan tells us that they wanted to build a company that did not require door-knocking in order to build the business. They wanted to build an internet company and provide it as an offering to a customer that doesn’t necessarily have a door to knock on. In order to achieve this, they identified the interested people through paid search advertising in Google. Continue listening to learn more.

Brand Guidelines

Ryan admits that it is expensive to build a brand; however, early stage customers are usually very forgiving, and as long as you are honest and clear with them regarding what you actually have, they typically give you a lot a latitude. This allows you to kind of experiment with what you are doing as far as the brand goes. The reality is that you don’t really have brand in the early days because nobody knows who you are until you build awareness. Continue listening at 11:47 to find out more of Ryan’s thoughts on building a brand.

Candor in Practice

In building a brand, Ryan previously mentioned that if you are honest with people, they tend to give you a lot of latitude. What he means by this, from a lean startup methodology, is you just go out to the customer and try to sell to them and see if they are willing to buy it. And then you make it clear that it doesn’t actually exist yet, but you appreciate their feedback and you are planning to build it in the future and we are happy you are interested. This is a great way for a small company to get feedback and find out exactly what people want before you go spending all of the time and money it takes to build the real product. Continue listening at 14:06 to learn more.

Business Success or Failure is Non-Binary

Ryan feels that the statistic that 90% of small businesses fail out of the gate is a major demotivator. He feels that since COVID, so much has changed in regards to life as we know it, and business success or failure means different things to different people. Nowadays, it is not necessarily just about raising money and building a huge product. Listen at 20:15 to learn more.

Pivoting Based on Feedback

Ryan explains that they had an assumption going into it that people were really concerned about the compliance of their business, which would be a motivator for them to work with a company like ZenBusiness, so that is how their message was initially directed. But what they found was that people were actually more drawn toward the more positive, inspirational messages, so they had to redirect based on this feedback. Listen at 22:21 to learn more.

The Psychology Behind Starting a Business

At 25:00, Ryan explains that there is a lot of fear behind starting a business. It is a leap into the unknown with a fear of failure, loneliness, debt, and more. However, people start businesses because they want to change their lives and improve their emotional wellbeing. This is where ZenBusiness comes in- to help them in this crucial startup phase to make the process easier and make them feel like they have a coach or a partner to walk through it with them. Continue listening to learn more.

What is Next for ZenBusiness

ZenBusiness has been fortunate enough to go through rounds of funding that have enabled them to grow and build more of the platform. Aside from growing their clientele, they are making a very significant investment in the platform itself. Learn more at 26:48.

Acquiring Investors

Ryan explains that they did a $4.5M seed-stage round, as well as had a lot of angel investors. At that stage, and even leading into the A-round, the investors are largely investing in the team. They realize the business might pivot in the future, but they are investing in a team that they feel is dedicated to building a successful business and will shift when necessary. Because of this, Ryan feels it is important to have a person on your team that has been through that journey before and has relationships in the VC community because that builds confidence for investors. Continue listening at 28:56 to learn more.

Entrepreneurial Gamesmanship

The relationship that you have with your investors is very important for a business going through rounds of funding. Ryan explains that it must be a very honest and real relationship. If you are coming up against the investment letter each month and it is bad, then that likely means you haven’t quite figured it out your product-market fit yet. Learn more at 31:50.

An Outsized Fear of Failure

There is a major fear among startup founders that they have raised all of this money against an idea that may not end up being viable for a business. “Continuing to pound the business idea when it’s not working, that’s probably a signal that something significant about what you’re doing needs to change.” When you are out there trying to find fit and find customers, if it becomes really difficult to find what you are looking for, it might not be the type of business that is viable for growth or warrant a lot of funding. On the other end, there are so many types of businesses that have the opportunity to be successful. Continue listening at 33:59 to learn more.

Biggest Piece of Advice When it Comes to Scaling

Ryan feels it is really important to have a predictable, scalable way of finding customers. Otherwise, the business is just difficult to scale. Ryan would encourage people to listen to the market and adjust accordingly. Learn more at 37:44.

Anyone that wants to learn more about ZenBusiness or get in touch with Ryan should go to or find Ryan on LinkedIn or Twitter; he is always happy to connect.  

Key Snippets

00:32 Go-to-Market Strategy

01:39 The Inspiration

03:40 Mapping It Out

05:40 Securing the Initial Customers

11:47 Brand Guidelines

14:06 Candor in Practice

20:15 Business Success or Failure is Non-Binary

22:21 Pivoting Based on Feedback

25:00 The Psychology Behind Starting a Business

26:48 What is Next for ZenBusiness

28:56 Acquiring Investors

31:50 Entrepreneurial Gamesmanship

33:59 An Outsized Fear of Failure

37:44 Biggest Piece of Advice When it Comes to Scaling

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