The Transcript

Making the Leap from School Teacher to Full-Time Food Blogger with Lindsay Ostrom

Jonny Nastor: This is Rainmaker.FM, the digital marketing podcast network. It’s built on the Rainmaker Platform, which empowers you to build your own digital marketing and sales platform. Start your free 14-day trial at HacktheEntrepreneur.com/Rainmaker.

Voiceover: Welcome to Hack the Entrepreneur, the show which reveals the fears, habits, and inner battles behind big-name entrepreneurs and those on their way to joining them. Now here is your host, Jon Nastor.

Jonny Nastor: Welcome back to Hack the Entrepreneur. I am so glad you decided to join me today. I’m your host, Jon Nastor, but you can call me Jonny.

My guest today is a blogger, food enthusiast, and entrepreneur. Along with her husband and business partner, they’ve created Pinch of Yum and Food Blogger Pro. My guest spent the last five years teaching elementary school by day and blogging about food by night. She always went back and forth about becoming a full-time blogger. But in June 2014, she officially made the jump to living this crazy, work-for-yourself-and-talk-about-food-online dream.

Now, let’s hack Lindsay Ostrom.

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Welcome back to Hack the Entrepreneur. Today, we have another brilliant entrepreneur. Lindsay, welcome to the show.

Lindsay Ostrom: Thank you. Thanks for having me.

Jonny Nastor: It’s my pleasure. Lindsay, let’s just jump straight into this.

Lindsay Ostrom: Let’s do it.

Jonny Nastor: Lindsay, as an entrepreneur, can you tell me what is the one thing that you do that you feel has been the biggest contributor to your successes so far?

Letting Go of the Scarcity Mentality

Lindsay Ostrom: Right off the bat, you hit me with a hard one. I think one of the biggest things that I’ve done, or that we’ve done, I guess I should say — my husband and I do these businesses together — is letting go of this scarcity mentality. It’s probably true across all different types of blogs and businesses. But with food blogging, it’s gotten increasingly competitive. There are more and more food blogs starting, and people who are rising up as these really, really talented people in the food space online.

It’s really easy to start to be comparative and competitive and to feel like “I’m not as good at this particular thing as so-and-so is.” For me, one of the most important things that I’ve done to be able to move past that tension is to get over this scarcity mindset, that there’s only so many people, and holding tightly to this idea that it has to be me, or I have to be the best, or I have to have the most followers. I think when you let go of that it frees you up to do better work.

Jonny Nastor: “Letting go of this scarcity mentality.” You are in, like you said, a very, very competitive space. Would you think that online, in these sorts of markets that you’re in — in a business podcast, I’ve entered a super, super heated space — do you think that maybe competition, as we know it or as we knew it, doesn’t even exist anymore?

Lindsay Ostrom: Can you explain what you mean by that a little bit more?

Jonny Nastor: To me, if somebody is going to read Pinch of Yum, they’re not just going to read Pinch of Yum. They’re going to read probably 20 other food blogs because they’re obsessed with them. People who listen to business podcasts, it’s not like, “Well, I have my favorite. I’m never listening to another one. When Jon comes out with one next year, I’m never going to listen to it.” They’re obsessed with it. People get really into what they’re into. Does that make sense?

Lindsay Ostrom: Yeah, for sure. That’s something we talk about a lot. I think it’s that same idea of, as we always say, “A rising tide lifts all ships.” Just the idea that as we get better, and as people around us get better, the industry as a whole becomes a better place for food bloggers and people who are doing this.

Like you said, the more people that are reading blogs, the more people that are making food and trying new recipes, in one perspective, it can seem like competition from one blog or website to another. It also is a good thing, because it fuels people’s interest in food. Then, they’re more likely to find us, because that’s the resource that we’re providing. I definitely think there’s truth to that.

Jonny Nastor: Excellent. You were a fourth-grade teacher. I believe you spent five years teaching, and on the side — or at night or on weekends — blogging, until you could finally go, just this past year, full-time. You had gone to school. You had gone through the whole process to get a good teaching job. What made you want to veer off of that path and try something else?

Lindsay Ostrom: I think our story with starting Pinch of Yum and building this as a business is so atypical, because it was never started with an intention to make it into a business or make it into something. When I started it, I never ever had the idea that I’m going to leave my teaching job and do this. It was like, “I have spare time on the weekends, and I like to cook dinner when I get home from work in the evenings.” It was this natural outpouring or putting on a display of the things that I was passionate about, this creative outlet that served as just a hobby.

I think that we saw the tension build on that as I loved what I was doing with teaching. I still am really passionate about education and really felt like that was meaningful work for me. When the blog started to actually become a thing that was earning money, and it was a business more than just a hobby, that’s when we started to feel this tension of “Okay, what do we really want to be doing?” We see this sky s-the-limit mentality with the blog, but I also loved what I was doing. It was really hard.

There was probably, I would say, a year and a half to two years of time when the blog income had surpassed the income that I was making teaching, but it was too hard for me to leave teaching. It wasn’t just about the starting of a business, and “I can’t wait to leave teaching and all that. Honestly, in a million years, I never would have guessed that it would have been here.

I know it’s not for everybody and it doesn’t work that way for everybody, but for us, that’s contributed to this success that we’ve had with the business because it’s this idea of the happiness advantage. I’m doing work I love, and I’m just doing this blog as a hobby. It’s a labor of love. I’m willing to work on it all the time because it feels like a hobby. It doesn’t feel like something that I’m a slave to this thing because I have to be. It was just something I really enjoyed. That was the primary motivation for me working on it for the first three to four years.

Jonny Nastor: “The happiness advantage.” I like that.

Lindsay Ostrom: There’s actually a book that I read that’s called The Happiness Advantage. I can’t remember the author off the top of my head. It’s a really good book. It’s this concept of the importance of investing in your own happiness and doing the things that you love and how positively that correlates with your performance in your work and in your life in general. A really good book. I’d recommend that.

Jonny Nastor: That’s excellent. You never thought that you would do this as a business, yet it’s not luck involved. Did you or your husband have experience in blogging? If not, where did you figure this whole process out?

Lindsay Ostrom: I think a lot of it is just trial and error. That’s actually contributed or been a huge part of why we’ve ended up building the businesses the way we have. When we started, there weren’t a lot of resources available as far as how you can make a food blog into a business.

I think my husband was really interested in that. For him, that was in line with the happiness advantage. He was very interested in that, wanted to learn about that, and had these ideas. But I had the actual platform, the actual blog for him to try these different things out.

Together, we started trying out these things that he was hearing, not necessarily about food blogging. The message we heard pretty clearly about food blogging was, “You can’t make this into your living. This cannot be done.” For him, he’s like, “I don’t know. I think we should try this through trial and error, and figuring out what’s worked and what hasn’t worked.

Sharing that, then, has really been a huge part of how we’ve built our businesses, and really valuing transparency: This is what works, and this is what doesn’t.” We know that’s valuable information for people, and we know that’s something that we can anchor our business around.

When we started, for me, I don’t even think I knew what a blog was or like that was a thing. It was really this marriage in more ways than one — because we’re literally married, my husband and I — but this marriage of my excitement about food and my willingness to show up every day and post and developing this platform, and his interest in the strategy side of it in terms of building it as a business. The coming together of both of those was how that process looked.

Jonny Nastor: Excellent. Trial and error — you seem to keep mentioning this. As human beings, as entrepreneurs, business owners, bloggers, whatever you want to call it, one of our greatest struggles is the fear of being wrong, making mistakes, and having those errors that could cause our businesses to fail.

Lindsay, can you walk me through how to go through one of these errors in your business and not have it completely side-swipe you so that you can move ahead like you need to?

Accepting the Tension of Being an Online Entrepreneur

Lindsay Ostrom: I think that it’s a really hard thing, but it s a really important mentality to have. For me, it’s not something I’m naturally good at, like overcoming the self-doubt. That’s not something I’m naturally very good at. I think people have this perception: “If you’re doing this, you must be really confident. You must feel good about every single thing that you do.” That’s really not the case.

For me, the key has been in accepting that tension. Not only accepting that, but saying, “Everything that we do, whether successful in its performance or not successful, everything is moving us forward in some way, even if it’s wrong, even if it’s a mistake, because then we’re learning from that.” We’re able to say, “Hey, look, that really flopped. Next time, this is what I’m going to do differently.” It sounds so overly simplistic: You just learn from your mistakes!

I heard a podcast once, I think it was on the Social Media Marketing podcast. It was about building a business and freeing yourself from this idea of making mistakes, and how making mistakes is a good thing. Bjork has this quote framed in his office, and I’m not going to remember who it’s by or anything at the moment. It’s about the idea that the award really goes not to the person who’s doing everything right, but to the person who is in the ring, actually falling down and getting back up every time. Even if you are failing, you’re actually succeeding, because you’re doing something. You’re moving forward, and then you’re learning from that.

For me, that’s a really hard mental shift, because my nature is very self-critical. I’m very much a doubter and a skeptic, but I think that’s super, super important. I feel like as I’ve been in this space more and more, I think that muscle in my brain has gotten stronger.

Jonny Nastor: Yes. I think from talking to so many people, as your husband says, that are in the ring getting knocked down, that it’s literally just a muscle that gets stronger the more you use it. I bet you if you thought about things that happened to you just in a given week in your business, like little failures and stumbles here and there that probably would have been so devastating three or four or five years ago, just to get over mentally, it gets easier. It really does. That’s smart. I like that.

It’s great that you have a team. There is literally such an awesome team that I’m sure if one person gets knocked down, the other one could be like, “It’s all right. Let’s just keep going. It’s cool. We’ve got this.”

Lindsay Ostrom: I think that’s a huge piece of that, being able to see a wrong as actually a good thing, or a fail as a positive and something you can learn from. I feel like part of it is just knowing yourself. For me, I know about myself that I’m not very good at that by myself. I always do better when I can talk to somebody about that or when I can process that somehow. It s like, “Okay, just give me 10 minutes to talk about it, and then I feel better.”

The interesting thing is for Bjork, he’s the opposite. He’s like, “I don’t really want to talk about it. I just need to think about this for a while, and just be on my own, which works out really great in a marriage. It’s just really good to know yourself and your strengths and weaknesses and how you process through stuff like that because you’re going to have to process through it. Figuring out what those things are and how you can do it to make those muscles stronger is really important. For me, it’s talking to people. That’s why it’s really great to have a team.

Jonny Nastor: Excellent. Let’s talk projects, if we can. Projects is a loose term that can mean any sort of new thing you decide to take on in your business. Whether it’s moving from Pinch of Yum to also Food Blogger Pro, or writing some new ebooks, or as you said prior to the call, starting a new podcast. What’s the process you guys go through, at this point, to determine what a new project is that you guys should go all into and focus on?

The Importance of Setting Timelines and Goals in Your Business

Lindsay Ostrom: That’s a really good question. Right now, my husband and I together run both businesses. I manage Pinch of Yum, the day-to-day. He manages Food Blogger Pro day-to-day. Our process is very...