Jenna didn't start her career as an entrepreneur.
She took a traditional route by studying finance in college.
After she graduated in 2011, there seemed to be only one path: working for banks, accounting firms, or consultancies.
That's what she thought success looked like.
"So I got a job in New York City and worked in consulting on risk assessments and anti-money laundering. More specifically, I was working with big banks to assess their risk of compliance."
She remembers thinking in her first week, "Oh my God this is what being an adult is going to be like. It’s horrible. Boring. Lots of time spent on Excel doing a lot of groundwork.”
When she realized that money wasn't everything, she chased culture.
As she says, "There was a lot of soul-searching."
She thought “You know what I want? A place that has a cool culture. What has cool cultures? I know, Tech startups.”
She notes no other research went into that. She got fixated on working in a tech startup, but when you go to school for finance and you're one year out of college, you have no skills for a tech startup.
They don't want you. You're not a designer. You're not a developer.
Still, she persisted.
And became the entrepreneur she dreamed about.
Today, she's the founder of Green Blender. They've shipped over 3.5 million smoothies nationwide and have 100 employees.
In this piece, we sat down to interview her unique entrepreneurial story.
Jenna like many other entrepreneurs started with a more technical background only to later shift to marketing. There, she'd find that the balance of technical and marketing skills made for a deadly combo. The intention to acquire these skills had everything to do with the purpose and culture of the company that would hire for them.
"You only know how to do Excel and that's not what startups care about. I thought, 'Okay, how can I make my resume better for a tech startup because that's the Holy Grail of culture?'
I convinced my company to pay for Sequel classes. I said I’d use it to recode these risk assessments that we had to do which were giant, bloated Excel projects. It was a nightmare to update anything.
To this day, I still use Sequel. It's a super powerful tool.
Still, I needed to get into a startup.
When you're in finance and go to school for business, the mentality at the time was everything should be private. Your Twitter feed should be private. Your Facebook account should be private. You shouldn't have an online personality.
When I jumped ship into the tech startup world, I saw people with hundreds of thousands of Twitter followers. They had these personalities online. They all had a side hustle and they were all doing online businesses and everyone was super plugged into the tech scene.
The startup that I got a job at was called Chartbeat. They do real-time data analytics for publishers. I convinced them that I should be a customer support agent. I got the role and immediately realized that I did not want to do customer support."
When Jenna jumped into startup life, she experienced, like many do, that not every startup is right for you. Sometimes it takes several. Fortunate for her, she found that path fast.
"At the Chartbeat, we could see the entire internet traffic which enabled me to understand how people move around the internet. It was my crash course in tech startup and hacking things together. So I started using more of my skills to understand what are the goals of the company.
'What do they hold most valuable?'
'Who’s driving the decisions?'
Then I realized I wanted a culture that had more work-life balance. I want to be friends with the people I work with and hang out with them after work. I also realized that culture wasn't everything and I wanted to care more about the product.
I was working on real-time data analytics, but at the end of the day, we were selling this idea of concurrence which is how many people are on your website at any given moment.
After a while, I felt like I was sitting on the internet trying to get more people to go to the Internet. It didn't feel authentic. I wanted to spend my time doing something more meaningful."
Most growth hackers don't even know they are one. When Jenna started her blog, she'd began to translate her technical skills into the world of marketing officially making herself a growth hacker.
"Because I got into the tech side of the internet, it opened my eyes that you can start your own business. I know that sounds straightforward, but people can run businesses and you’re a person and you can just do it if you have an idea. Just create a website and talk about it.
At Chartbeat, I started a blog about health and wellness called Urban Fitopia. That was in the early days of Tumblr and I became one of the fastest growing ones. This was around 2013.
That was my first foray into growth hacking.
The number one thing I learned in building an audience is consistency is king. You have to create content on a schedule, then publish it regardless of whether you think it's perfect. You have to just put stuff out there and see what the response is.
Number two is building relationships. I met many awesome health and wellness bloggers online based in New York City, and then met them in person. This led to partnerships.
Then three would be don't solve for your future problem, solve the problems at hand. You have to boil down what your steps are.
'Do you want to grow your blog or do you want more followers?'
'Do you want to sell a product?'
Stop worrying about what happens at scale or 'how do I source 100,000 apples?' or anything like that.
You have to say,
'How do I get that first customer?'
'Get the first five customers?'
'Maintain those customers?'"
Unlike many employees, when Jenna lost purpose at her job, she picked up another one fast. This helped expedite her career and learnings faster than most people.
"When I was at Chartbeat, I got an itch to work on something that had more importance to people's day-to-day lives. Because I started this fitness blog, I talked to many health companies on the internet. One of those companies, I started tweeting at and we started having conversations online. This company is now called ClassPass.
They’re a gym membership for boutique fitness studios. They offered me a job on Twitter. I became their first marketing hire. That’s when I went from real-time data analytics and being a product analyst to being a full-time marketer.
I got my crash course in online marketing.
'How do you blend this idea of a tech company that's online with a physical experience or real life experience?'
'How do you get people to do what you want them to do?'
'How do you grow in engagement?'
I loved my time there, but I wanted to be in the driver's seat."
The best companies are never intentional. They happen because you're playing with your passions. For Jenna that was health and wellness.
"I was thinking about health and wellness and my boyfriend at the time (we’re married now) was working at another tech startup. We were talking about how technology can help you improve your health. We got a blender and started making smoothies around the same time. Then one day he said, 'We should just send people smoothie ingredients to people's houses.'
The problem was obvious. Nine out of ten Americans don't eat enough fruits and vegetables, not because there's lack of information online or that you don't know you should. It was convenience. That’s why we were seeing meal kits becoming popular.
People were becoming more comfortable receiving food in the mail. We did some research and found that 82% of US households own a blender. It's the second most popular appliance in someone's kitchen. Every ten years the whole country buys a new one.
The data said this would be a great opportunity.
Amir and I are firm believers of The Lean Startup mentality. So we created a landing page that had our value prop on it.
It said something like 'Smoothies delivered. Sign up here.' We had a simple optin for their email and zip code. We drove five hundred dollars of AdWords traffic to it.
Anytime someone tried to sign up, we would say 'Sorry Green Blender isn't in your area. Try back later.'
We were just trying to see if we could get someone's email address and how much would that'd cost. We got around 150 emails on the list.
At the time, we were flying to Tahoe for a ski trip and I looked over at Amir and said, 'Okay, let's just get this done.' In flight, we set up an LLC on LegalZoom and a business bank account.
We thought 'Let's send them an email and see if they buy.' So we sent an email that said, 'Great news Green Blender is in your area, sign up here to get smoothies delivered.'
Five or six people bought and then we were like, 'Oh shit. We have to produce this idea.'
We went to the grocery store put boxes together and got on the subway and delivered them to people's houses."
In startup early days, founders have to do the unscalable. There's no way around it. You're wearing multiple hats whether you like it or not. Many times you're taking the most unconventional routes to get the work done.
"In the early days, you're doing everything so you don't have the luxury to hire somebody to work in your business so that you can work on your business.
Some of the things that we did were not scalable. We were shipping boxes out of our apartment for the first couple months and it was winter time. We had them in our second bedroom and we would turn off the heat in that second bedroom and open the window. That was our walk-in cooler for all this food.
Then we’d have around 15 contractors come and pack boxes with us. It felt like a drug operation. But we were pushing fruits and vegetables. We went and bought food at the grocery store and then packed them into boxes to understand what ingredients shipped well and learned about minimums and understanding what types of companies even sell food to grocery stores.
I remember Googling, 'Where do grocery stores buy their food?'
I took pictures of trucks parked in front of Whole Foods and called the number on the truck and asked, 'What do you guys do? Will you sell produce to me?'
The point is you don't have to be an expert to get started. You just need to solve for the problems at hand and not worry about what happens when you're shipping 10,000 boxes.
Because you have to get there first and to get there first.
However, you need to do it."
As a founder, even though you wear many hats, the goal is to take one off at a time. If you can't free yourself up, then you can't innovate, hire, and build the business you're capable of.
"The number one thing that I can think of is delegation. It's still the main issue I have today. It’s understanding when I should pass something off to somebody else and when I should hold it. An example of what I mean is for the first year and a half, I took all of the photography of all of the smoothie recipe pictures and would do it all at once in my backyard because that was where the lighting was best.
No matter what the weather was, I'd shoot, edit, and put the images online. Doing all that stuff took two days of work.
Then I was looking at a list of things that I need to do to improve Green Blender. One of the things was to get photography off my plate. It was an argument with myself about how important it was that I needed to do it because it’s the essence of the brand. Then when I finally got it off my plate it was a sigh of relief.
Today, our photographer does it one hundred times better than I ever have done it. She has more time to think about the actual recipes in the format of the photography. The learning lesson is nine times out of ten, someone else will do it way better than you.
That’s why it’s important to make sure that every week you spend some time thinking about where you spend all your time.
Being aware that sometimes people use 'like this is what I do' to hold onto these already solved processes as a form of procrastination for not having to solve hard problems that haven't yet been solved in your business. That’s the point of you being the founder. You're the one that is moving this agenda forward.
You're running through brick walls and you're trying to solve problems that have never been solved before. If those are the problems that you don't have time to do then you need to get stuff off your plate or else your business will die."
Most startups fail because the founders can't stay motivated. They burn out from failing too many times. On a long enough timeline, most startups can be successful through pivoting. However, few have the patience. That's why many founders sell their company or just give up when people least expect it. To keep going, you have to be passionate about what you do.
"Part of the business that I like is that we're helping people eat more fruits and vegetables and live a healthier life. It's refreshing to come to work and solve these problems. It makes a lot of the hard decisions and sleepless nights worth it.
Subscription businesses are interesting because you have several clear levers that you need to improve. There are several metrics that you don't have to find.
'Should we make the UI easier?'
'How do we improve lifetime value?'
'Should we launch new products to do that?'
Having clear goals is really satisfying for me. So lifetime value, retention, customer acquisition and then your margins. The actual steps to improve them are not as clear but your end goal is always very clear."
One of the most admirable parts of Jenna's story is her ability to run a company successfully with her spouse. It's often a rarity that a marriage can work in and out of the office. Jenna breaks it down how it's not magic; instead, there's a reason it worked well for them.
"I have done a lot of thinking about what made it so successful to run a company with my spouse. Number one is that we have complementary skills. I do marketing acquisition, financial modeling, and he is a developer. He works on the product roadmap and operations.
We come together and talk about what we've decided and then go apart again and start running the operations or the marketing or whatever it is. If we were both marketers, then we’d have a lot more friction.
In the beginning, it was difficult to understand how each other worked. I'm an early morning person. I love to run before work. I like to get shit done early. I want to start my meetings on time. I'm very type A.
Amir is not so into waking up early.
He works late at night.
He's a little more chill.
It’s important to discuss how you like to communicate when you're at work. It's a totally different environment than when you're just hanging out at dinner.
Right now we're doing smoothies which I like to say is the gateway drug to healthy living.
Where we're going next is asking,
'What else can we do to help people improve their health on the margin?'
We’re looking at where a blend fits into their daily routine."
When Jenna started her company, she took a long-term vision. Unlike most entrepreneurs who aim for quick wins, she built a marketing foundation that could stand the test of time.
"At Chartbeat, I saw everyone's traffic and how it changed.
Some websites had all their traffic come through Pinterest and some from search. This gave me insight into how powerful it is if you can rank with keywords. So we had a content strategy and a social strategy before we even had a single product.
We posted to Instagram to drive our social traffic, created content, and published thoughtful articles that would rank for certain keywords. SEO is one of those things that's a slow burn. You can't just say, 'Now we have time for SEO. Let's flip the switch and like spend $100,000 on it.'
That's not how it works and you have to work on it every single day for four to ten years. There are hacks and stuff but the secret is to be consistent and thoughtful about what you post. Make sure it’s all tagged correctly. It has great rich content. That's there are backlinks to all the images and everything is titled correctly.
Most of our traffic comes through organic search. That's been helpful for us in prospecting. Then you can retarget all of that traffic and it only keeps growing the more content you put out.
You need to be nimble. What worked last year is not going to work this year and don't cry about it. Assess your environment and figure out where the opportunities lie. You have to do that every single day. You can't rely on the status quo.
We try to build a culture of learning and taking risks. It's sometimes difficult because our product is cyclical where we send boxes every week. Every week we are doing the same thing but different because we’re always trying to improve.
We spend time researching where's all the traffic is going.
Where's everyone's attention being spent."
Being an entrepreneur is far from easy. In part, because you never settle.
"You're never going to feel like you've made it.
That's the nature of being a successful entrepreneur. You always have this anxiety You think 'Oh my God, I need to grow faster or we need to be doing something different.'
It’s a good feeling to have.
It ensures that you don't become obsolete."
Today, Green Blender is helping hundreds of thousands of people become healthier.
As Jenna expresses, it's more of a movement than anything to help people enjoy their lives.
Because when all is said and done, what we're left with is our health.
She's on a mission to ensure everyone knows that.
Most importantly, that they take action today.