Rebecca Woodcock – Cake Health 2 of 2

"Founders should learn how to invest their time." Cake Health is a web service that helps users understand and manage their health care.

Matthew: We know founders face unique challenges when they decide to build a company. What was the hardest part about building Cake Health and how did you overcome this obstacle?

Rebecca: Finding that good, solid partner to work with. Not only talented, but someone you can trust and who can really move that ball forward. That was what took the longest to find and is, I think, the most critical to success, if you don’t have that right partner. And that’s the struggle that every founder will have in the beginning, is finding that right person. And I think that was the hardest part for me, too.

Matthew: Since you’ve been in operation, what have you learned about your business or your users that you didn’t realize before?

Rebecca: We’re constantly learning things about, not only our business, but our users. Since we’ve been in beta, we’ve learned who our passionate users are. They’re oftentimes new parents or parents-to-be. The surprising thing is it could even be the dad. It’s not even the classic mom example. A new dad or a dad-to-be is also as passionate about our product as a mom, right? They’re having a lot of bills come in and it’s oftentimes the first time they’ve ever had to deal with all this paperwork. They could have ignored it before. So, that was a really interesting learning.

Our business evolves so much just week to week, month to month. In startup life and in early stage startup, one month is a lifetime in your business, right? So, if you talk to me at the end of one month, you’ll see definite changes in how we’re crafting that model and that business model.

So, what we thought we would go to market with as a business model has changed. I can’t describe everything that we work on, but we’re constantly course-correcting.

Matthew: Lots of people admire entrepreneurs because they appear to make starting companies look easy. We know it can be really difficult. My question for you is what talents or skills come easily or intuitively for you? What has been difficult? How do you manage that?

Rebecca: See, starting a company is not easy. I would say the things that were the most difficult for me were gaining that moment. When you first start, oftentimes there are so many questions that you have and so many unknowns. And there’s an insecurity level that comes around all of that. It’s often in that idea stage. And so, as you start piecing some of those things together in the puzzle, and it could be just knowledge about the market, it could be part of the product, it’s often part of the product as the product develops, you can become more confident in what you’re doing. And so, these unknowns and the insecurity that comes with it, just overcoming that is a huge challenge. But, keep going. Just keep going. It’ll slowly piece together. That would be my advice. Never give up.

So, that was a big challenge for me, just gaining that momentum and just building it to a point where I can have that confidence to really move the ball forward.

What came easily, which was surprising for me, was the ability to create a lot of hype. And I’m not sure why or where that came from, but we’ve been fortunate in being able to position ourselves at the right place at the right time and create a lot of hype around what we’re doing. So, that was surprisingly easy.

For me, my own personal skills; because I have this research background, just taking abstract data ideas or trend ideas and seeing how they converge, that comes easily to me. But, what’s difficult is explaining that to someone else who may not understand that. So, while I can absorb it and process it, explaining it is sometimes not the easiest thing.

And project management is a difficult one that I think I’m constantly learning. And as we grow more moving parts and moving pieces, that’s something that I can always improve on.

Matthew: What bit of advice do you wish you would have known before launching Cake Health?

Rebecca: I still need more advice on how to better manage and guard my time. Because as an early stage start-up, you only have a handful of people; you, your co-founder, maybe one other person, maybe a couple of other people. And anything you do will have an impact on your ability to move your company forward. So, being careful and knowing how to spend your time. Even with investors because they can suck up a lot of time, especially when fund-raising. There are just going to be a lot of opportunities at some point and just knowing how to filter that and identify it, that’s something that I’m constantly battling. So, I wish I had that advice before and I wish I had that advice now. So, I would say seek that.

Matthew: What advice would you like to share with our audience about launching or building a start-up? If you had to distill it, what are the key elements?

Rebecca: So, for building a start-up, in my opinion, the key elements are finding that right combination of people, the team, your co-founder. It’s so critical. The product and just moving that ball forward. Anybody and everybody have ideas. It’s all about execution. So, start executing, iterate quickly. And the third would be get lots of feedback constantly. So, from users, from people in the industry, from investors. All of that will shape your product and your business model and your company, and that will help you move forward.

As far as launching, I would say try to find your advocates. Find those groups or people who will just be your champions. And it could be through an incubator. It could be through investors or people in the industry or people who are willing to just promote you and help you. Any way that you can. I would say when you’re launching, just having that kind of visibility and people who are pushing your product for you. Those advocates are so key.

Matthew: Before we close, we would love for you to give our audience your vision for Cake Health and how you hope it will change the world.

Rebecca: For Cake Health, whenever you need to make any decision about healthcare, whether it’s about a plan or whether it’s about getting a service or how you should be spending your money, your flex spending, any decision that you need to make around healthcare, we envision that being made through Cake Health. So, we’ll have tools that will help you make forward looking decisions, and not just historical, and make it very task-oriented.

It’s not a website that is a news website where you’ll just wake up in the morning and see what’s going on there. But, we want to make it very task and action oriented. What should you be doing? Updating you on how you could be taking care of yourself better and the decisions that you should be making around healthcare and help you with those.

Matthew: Rebecca, it’s been a pleasure having you as a guest on FounderLY. We’re rooting for your continued success at Cake Health. For those in our audience who’d like to learn more, you can visit their website and join their community at

This is Matthew Wise with FounderLY. Thanks so much, Rebecca.

Rebecca: Thank you.


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