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Running Your Business: A Tale of Two Entrepreneurs (Episode 74)

Evan Cummack is the CEO of Fin, a company shaping the future of work.

Fin Analytics is a cloud-based, comprehensive measurement platform for operations that helps with running your business, driving efficiency, and reducing operating expenditures through data-driven process improvements.

Prior to Fin, Evan was a General Manager at Twilio, the fastest growing SaaS company in history by revenue. Evan joined Twilio in 2011 as one of the company’s early employees and helped to shape the company’s unique “middle out” sales strategy, as well as led the development of new products and businesses over the course of a decade.


Twilio was started in 2008. Evan joined towards the end of 2010, as the company was raising series B financing, but still had a very small team

Evan was a founding member of the go-to market team. Within a few days, they went from a relatively self-service, basic company to an active enterprise solution, putting sales into motion by taking their product to market.

The idea for Twilio came from one of the founders, who had worked on various projects prior. In each of those cases, there was a problem that he was trying to solve as a software developer. Every function had quite a bit of exposure or experience with software development, and as a software developer, he felt that he should be able to build things. At that time, telecommunications phone systems couldn’t do anything, and it was dominated by companies that would install hardware and configure it for you.

Cloud computing was emerging at the time, AWS was growing very rapidly, and it seemed possible for the first time to take a closed off network that carries billions of dollars of economic value over a year, (the telecommunications network), and discover ways to expose that to the millions of software developers around the world who will be able to do creative things with it.

That was really the genesis of the company, and that philosophy stuck with the company for a long time. Eventually they grew to a point of expanding into other types of products that were not strictly involved in telecommunications, but it was enough to keep them busy for a number of years early on.

Savannah Peterson

As a Forbes 30 under 30, Savannah has an incredible repertoire under her belt. 

She’s worked at Fox Sports, was the Director of Innovation Strategy at Speck Design, among other accomplishments, and started Savvy Millennial. Now, she teaches entrepreneurship and other relevant topics for running your business at Stanford, NYU, PACE, and Xavier. 

Savvy Millennial 

In short, Savannah and her team want to make the future less scary by building community around new technology.

Specifically, they work almost exclusively with series A, high-growth startups who are looking to get to their first thousand or 10,000 customers.

Using a variety of carefully crafted tools and techniques, Savvy Millennial is a company that helps up-and-coming businesses build their brand, market themselves to the correct audience, and create their unique culture and community.


For these two professionals, community is considered to be their first defensible asset. If people are passionate about the solution that you provide, they’ll ride with you through pivots and through the ups and downs that every early stage company has.

To achieve this loyalty, it’s important to be engaging, transparent and authentic about user feedback, and keep consistent communication with your early customers while running your business.

When a company chooses to build up the community around their product, reinforce why that product adds value to that person, and encourage them to share that story, not only are they changing the size of their marketing teams, they’re also tapping into the key to achieving a repeatable enterprise situation.

There are two important realities. The first reality is that everyone wants to work as efficiently and intelligently as possible. The second is that every single human being works differently. We all have different processes for how we use programs, log into zoom, or work in a document, and when we are aware of those processes, we’re able to figure out how everyone can work more efficiently and raise the water level together. 

This is what the team at Fin hopes to do.


Fin is the answer to the technology bottlenecks that are holding people up, causing frustrations, or causing problems. Starting with the understanding that most enterprise work today happens inside a web browser, Evan and his team decided to start instrumenting the browser itself.

They started by seeking to understand all the different applications that people use during the day. What are the tasks that they’re completing? What are the workflows that they’re following? How are they using these different applications to make these decisions?

Fin uses UCI laid on top of collected data to gain insights, and make the best recommendations. 

Fin allows you to perform the studies you need without sampling. You’re actually looking at the entire population, the entire data set of all work being done, and using that to make inferences.

With the explosion of software as a service, it’s completely changed the way we work: instead of the CTO, or someone dictating the software you’re going to use and exactly how to perform certain tasks, an enterprise will simply go and find their own tools.

It’s great for entrepreneurs, because you can very easily create these highly specific SaaS programs, but it makes it harder for an IT department or an enterprise to actually understand what is being done/used on a regular basis.

Applications for Running Your Business

With the current situation being as it is, Fin has started providing a tool that identifies how people are working, no matter where they are. This led to some incredibly important insights.

First, it provides information on wifi and computer performance, which means they can provide insights about a particular cohort of workers who may not be delivering as much as everyone else simply because they’ve got slow internet. 

For obvious reasons, this prevents conflicts, miscommunication, and higher retention rates. Rather than looking at the numbers and making undeserved cuts, you can invest in giving these people better technology to use at home. 

Evan operates on the assumption that all team members want to do their best work, and therefore removing roadblocks, whether that’s bad software, bad networks or bad training, is an objectively helpful thing to do.

Addressing the Big Challenges

Still, there are always certain challenges that pop up, regardless of the stage you’re in, or the measures you take to gain experience running your business.

#1. Onboarding

How do you make it simple for people to onboard? 

When Evan left Twilio, they had around 8 million customers. Because of this, they obviously needed a model that was self-service oriented, or at least self-service compatible. 

The bottom line is, you can’t be in the room all the time, and your customers need to be able to trial your product in order to make a decision to use it. This has to happen whether you can be in the room or not. From Evan’s perspective, facilitating that aspect of the community to be as hands-on with customers during the onboarding process as possible, even if it’s a relatively rapid process, is a huge part of successful community and product design. 

It takes a couple of hours for the team at Fin to onboard most customers, but they are still actively involved in that. They might not get to meet all of their customers, but they get to understand their problems. 

When it comes to scaling, they are investing heavily in building tools that allow people to onboard themselves. One of the nice things about the technological approach that they’ve decided to take towards this particular problem is that they are focused on things that happen inside a web browser. This lowers the technical barrier, versus some of the other practices that have been used historically.

#2. Retaining

The truth? Both Savannah and Evan claim people stay for the community.

One of the key moves that Finn made in the early, pre-pandemic times was hosting dinners and inviting the community to them. This is where many of their initial customers actually converted from. Their customers feel like they have friends on the team, and everyone has personal access without overwhelming the staff. 

When it comes to customer solutions, they have a strong rapport with their customers because they’re very candid.

As they are expanding globally, they look forward to bringing their community together, both virtually and in-person. In fact, they plan on creating a show around it. 

The tactic of overly aggressively trying to fit a product to a customer that was never a great fit in the first place will always lead to losing members of your community. 

Tips For Running Your Business

First, talk to your customers early and often.

Think about the community that surrounds your business, and build yourself up from that.

There is a healthy tension that always exists between the marketing community and product, but the reality is, if you build it and it’s just sitting there, they won’t come. 

Talking to your customers about the good stuff as well as the bad, and learning how to take constructive criticism even when your loudest users are not actually correct in their assumptions, is so critical.

Look for the needs. Don’t just make another thing to make another thing: innovate, don’t iterate.

According to Evan, a common mistake made by those on the executive level is self-validating ideas.

This happens when you’re “talking” to your customers and getting feedback, but what you’re really doing is trying to validate that you are correct. Whether on purpose or not, you end up asking loaded questions or interpreting things in a way that confirms your biases. 

Instead, learning to actually listen to any problems, or improvements, can make a huge difference early on, and is an underused resource. 

Along the same lines, it can be quite easy to get overwhelmed with managing all of the various social networks, and their unique systems. Comparison is a poison: 

“There’s so many people doing this already!” It’s kind of like Instagram, where people show the most polished, perfect images they can, often missing the more realistic parts of life.

For beginners, there is a tendency to do the same thing: it’s easy to look at all these companies, their techniques, and get distracted by their success. It’s unhealthy for your personal life, and it’s just as unhealthy for the business.

The better thing to do is focus on the specific problem that you’re solving within your own team. Talk with your customers, understand their problems, and make sure that you’re solving it in a way that builds rapport and loyalty with your clients.

Finally, give yourself a mental health break.

Running your business, scaling a business, everything that we do is incredibly hard. If you’re reading this, you’re probably doing something very challenging that may or may not have been done before, and you need to give yourself credit for that endeavor. Part of that means taking care of yourself, and giving yourself the grace to continue innovating and making mistakes.  

If you don’t put your own oxygen mask on first, you can’t help others. If you haven’t polished your current process, you can’t go get new customers. You can’t close bigger deals and you can’t hire the best team possible.

In the end, we are holistic human beings. We’re working hard to make the world better, but don’t forget that you’ve got a soul, a heart and a mind and a body that needs to be nourished.

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