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Lemons into Lemonade: Heidi Weinberg

If you're part of the fashion community, chances are you've already heard about the incredible Heidi Weinberg, aka Sew Heidi. She's not only a talented fashion designer but also an educator, podcaster, and serial entrepreneur. With experience in every aspect of the industry – from creating her fashion brand to working in-house and freelancing for other labels – she's truly a force to be reckoned with.

But that's not all. Heidi is also a pioneer in online fashion education. In fact, her freelancing course was the catalyst that led two of my team members to reach out to me. Talk about serendipity!

After being featured on her Fashion Designers Get Paid podcast, I finally had the chance to flip the script and interview this remarkable woman. Getting insight into her journey and her successful businesses was mind-blowing. She's a true inspiration.

So get ready for an exclusive look into Heidi's incredible story. Buckle up and prepare to be inspired!

Heidi Weinberg wearing a black leather jacket holding her laptop with a word bubble saying Hi, I'm Heidi

You’ve had a unique entrepreneurial journey with a few different ventures, from starting your own brand to freelancing and now being an educator for freelancers. Can you talk about those experiences a little bit?

“I essentially started with having my own fashion brand, which was a dream of mine. I don't have any regrets about doing it, but, if I could rewind, I would do some things differently. Ultimately, it was much more work and less money than anticipated. Which sort of leads me into freelancing. It was a better match for me. I found that I could do the parts of the process that I loved. I got to design, develop, and see products manufactured without having to front any money or deal with inventory. Now, I’m an educator for freelancers. I see this as another way to sell my skills and expertise. I settled on the educational component because I was so passionate about my career as a freelancer and how much freedom it allowed me.”

K: Education is so important in this industry, and it’s challenging to figure out if you don’t want to go the traditional route of going to school for fashion. Even if you DO go to school for fashion, it’s still a challenge because there’s so much on-the-job training you get that is what prepares you for the reality of it all. There’s a lot of smoke and mirrors here, and I’m sure your students are super grateful for you to clear the way for them!

Were you always interested in starting your own company? What inspired you to start your own business?  

“Yeah. I think it's been in my blood since I was a kid. My dad was an entrepreneur. My brother and sister are both entrepreneurs. Looking back, I can remember setting up lemonade stands as a kid. I was always that kid that took it to the next level. I was selling brownies, and otter pops on the side.  As an upsell, you could even pay 25 cents more if you wanted whipped cream and another 25 cents if you'd like sprinkles.  It's hysterical to look back at. I never really strategically thought in my head I'm gonna start my own company; it was just something I did very naturally."

K: I LOVE the upcharge on the brownies for sprinkles or whipped cream. You definitely have some childhood stories that remind me a little of my own history — starting with entrepreneurism at a very young age is probably part of why I am who I am today.

What inspired you to transition from running your fashion brand to freelancing?

“It was really just the exhaustion and lack of money. In my second or third year of running my fashion brand, I brought in $40,000. I was 20 something and I hadn’t gone to fashion school and I had no idea what I was doing. I thought that was a really big success. The problem was that of that $40,000, literally, nothing went back into my pocket. All of that money went back into production, inventory, and marketing. I just got really turned off by the high cost and inventory management. I really fell out of love with it.”

K: The early days are never easy — I’m not surprised that your revenue went right back into the business for several years before you had that eureka moment that this wasn’t your favorite part of the fashion biz. Like they always say, it takes 10 years to become an overnight success. So many people want to be wildly successful right out of the gate, but that’s not the most likely outcome of a new fashion venture. If you want to make it profitable, it will take a lot of time, money, and energy. It’s good to hear a story about someone who didn’t feel like they needed to keep going in the same direction to find success; sometimes we have to zig-zag.

Can you share a pivotal moment that influenced your decision to become an educator in the fashion industry?

“I was working in my “dream” fashion job that was really not so dreamy. I landed the job because I had really strong Adobe Illustrator skills. I had gone to school for graphic design, and as a graphic designer, we learned Illustrator very very well. I quickly realized that everything in that company was done in Adobe Illustrator, from fashion flats to line sheets. My co-workers and interns who had gone to fashion school and been formally trained had no idea how to use Adobe Illustrator. I went home and told my then-boyfriend, now husband, “People are not learning Illustrator, and it's crazy. They're doing things really roundabout ways and they’re not teaching it in fashion school.” He told me I should make some videos and put them on YouTube. I was like, “Whaaaaat?!” This was in 2008, so that was kinda new territory. Eventually, I put up a few videos on how to do fashion flats and how to draw for fashion design in Adobe Illustrator. And then I kind of forgot about it. I logged into my YouTube account a year later and I had $300 in ad revenue and a bunch of people were watching my videos. So I thought, okay maybe this is a thing. My entrepreneur-wired brain thought, “Oh, I can make money doing this”. That was the first domino.”

K: So cool that you just set it, and forget it and found that it was successful without much effort. That had to feel really gratifying!

Heidi Weinberg wearing a leopard print sweater holding headphones and sitting on a stool in front of a neon green background.

What was the beginning of starting Successful Fashion Designer like? Did you have a hard time getting started, or did the pieces fall into place? 

“It started with creating those YouTube videos. When they started to take off, I thought I would turn this into a workshop. I found a friend who wanted to learn Adobe Illustrator, and I created a rough outline for a course. I sat down with her at my house, and we went through it over a couple of weekends. I had my first beta student. Then I started promoting within the small fashion community in Denver. “

“In 2013, my husband and I moved to New York City. There I connected with a company and taught in-person workshops. In 2015, I started my website, so I could begin teaching online. I didn’t want to teach in person anymore because I wanted to reach more people. Also, people weren't retaining the information. They would come back two weeks later and have to re-learn. It needed to be in video format, where people could go through it over and over again at their own pace. I remember waking up in the middle of the night and I had dreamt of the name Successful Fashion Designer. I bought the URL because I knew it would be bigger than Sew Heidi. That was the beginning of it turning from a side biz teaching workshops to structuring it as a full-time business.”

K: It’s funny how much comes to us in a dream! 

Was it scary when you first went out on your own in your many ventures? Which experience was the scariest? How did you get started? 

“Yeah for sure. All of these ventures have been scary. I remember when I got a job right out of college as a receptionist and I hated life. I had always been an overachiever. In college, I was an honor student, had a really big academic scholarship, and I graduated cum laude. But, when I graduated, I just settled for a receptionist job. I was so bored. In the background, I started building my fashion brand. I was sewing nights and weekends and getting everything prepped to attend markets. At first, I didn't have great success until one market where the clientele matched up perfectly with what I was selling. I made $2,000 in one weekend. Which was a lot considering I was only making around $18,000 at my job. I thought screw this, and I talked it over very extensively with Marc, and he gave me the courage to quit. He's a leap-of-faith guy. He told me to jump and the net will appear. So, I quit. I remember being super terrified, but it turned out to be great. I learned a tremendous amount. I will also preface that we were young. We didn’t have a child. We lived in a home that had a separate apartment in the basement that we rented out. We had very low overhead. He had a stable job. We were able to take a risk."

K: Jump and the net will appear is a phrase I’ve taken on a lot as I’ve grown my business. Sometimes you need to be afraid and do that sh*t anyway. It allows your mind to come to terms with the fact that you can figure it out. The leap forward towards something you dream of can be SOOOOO inspirational and motivational for people. If you’re scared, it’s a good thing most times in life (unless someone is chasing you or you’re falling from a tall building :P) otherwise fear usually means you’re working on something that matters, something you care about.

"Then, I landed my dream job as a fashion designer about 2-3 years later. I was burned out from doing my own brand. I started teaching and ultimately quit that fashion design job because it got so toxic. Going out on my own as a freelancer felt scary, but deciding to go out on my own got easier and easier each time. I think it's a little bit of a muscle that you strengthen over time. I also think if I look back on my career, the biggest jumps I’ve taken and the scariest jumps I've taken have been the best in the long run. They're really scary at the moment, but looking back, that was the domino that led to the next big thing. I think I've taken some risks that were maybe not super calculated, but I think those big risks are required in a life like this.”

What challenges did you face when making the shift from designer to educator, and how did you overcome them?

“I'm not sure I really faced any specific challenges because I was running both of the businesses in tandem for almost four years. My online business was slowly growing and started gradually not taking on new freelance clients and only keeping present ones. Eventually, I decided I was officially done with freelance work. I don't really think there were any specific challenges with that. It was more the decision to give up that “security blanket” that I had felt as a freelancer. But I don't even know if that is really accurate because I have spent so much time building up my online business. I had invested in courses to learn how to sell, how to do launches, how to host webinars, how to write sales pages, and how to write sales emails. I felt really strong. I had some really big wins by that point. I had achieved 5 figure launches. So, I don't really feel like it was a huge challenge. It was more of a really slow transition over multiple years.”

K: Wow, it's clear that you put a lot of thought and effort into your transition. Your approach was so smart and gradual, it felt completely natural and not forced at all. I really admire the fact that you mentioned the courses you took. I'm a huge advocate for lifelong learning. In fact, when I decided to explore education and mentorship, I also took courses to learn about creating online courses, hosting webinars, and writing effective sales emails. Learning from others is so valuable because it helps us avoid making the same mistakes they did.

What is the biggest failure you've experienced in your business? What did you learn from it?  

“During my freelance career, I quoted a project for about $5,000 and when I finished the project it ended up being much more work. It should have been a $10,000 or $12,000 project. I’m not even sure I would consider it a failure. It was a great learning opportunity. The client was really rushed with the project so I rushed with the proposal. I didn't ask enough questions and I made some assumptions. I learned to take my time and thoroughly vet the project before I rush into a proposal. After I finished the project I had a nice chat with the client and said thank you so much for the opportunity to work with you. I’m really happy about how this came together. I want to let you know that I really underbid the project. It’s something I take full fault on. I'm happy to have done it for the $5,000 but I want to be transparent that going forward that is really not the price so next time you need help with something I don't want to blindside you with a really big price tag. They were very understanding and were very happy with how the project turned out so we talked about what general numbers might look like in the future. I ultimately wound up working with that client for a really long time at higher rates. So, I think the lesson is if you make a mistake, whether in pricing or you deliver late, own it immediately. Say sorry and take responsibility. Then set expectations for how you're going to prevent doing that again in the future.”

K: I completely understand where you're coming from. I recently made a mistake and accidentally gave a client an incorrect quote. As soon as I realized my error, I contacted them and explained the situation. Thankfully, they understood, agreed to revise the contract, and agreed on the adjusted rate. It just goes to show that people truly value honesty in business.

What's the best advice you've ever been given in life or business? 

“I would say there's two things. One is 80/20 and that is 80% of your results come from 20% of your effort. Over time I've really tried to be conscious. I'm still not perfect at it because I tend to over-tweak things. I always want to do an exceptional job but determining when you’re doing frivolous things is a hard line to navigate. The other thing I would say is about your comfort zone. If you’re not feeling a little bit uncomfortable then you’re not pushing hard enough. I push this on my students all the time when it comes to pricing, going after dream clients, and asking for what you want. I constantly have to remind myself too. You should consistently be a little bit outside of what you know. Go beyond where you feel comfortable. I think that is where we have the biggest and best wins.”

K: Are you inside my head? Haha! I’ve been given this same advice and now preach it myself. I always have a million business ideas running through my head like learning Clo3d, hosting workshops, or adding new services - but I have to remind myself to focus on the 20% that will truly make a difference for my business. I also agree that getting out of your comfort zone is crucial. I’ve seen this often with my intimates brand, iteration, that I’m building. It’s new totally territory for my business partner. I constantly remind her that it doesn’t have to be perfect, done is better! We will learn as we go, and sometimes you just have to leap. You’ll never be “ready” and if you feel “ready”, you’re already too late. 

Heidi Weinberg wearing a black leather jacket holding her laptop standing in front of a neon green background.

What's the most recent lesson your business has taught you?  

“I have not been present on LinkedIn for many years and I finally got on there just a few months ago in September of 2023. I'm still finding my feet on there and trying to post consistently every day. I'm experimenting with different types of posts and different content trying to figure out what resonates. I've put some posts out that were arguably not in my lane. Around Black Friday a lot of people in the sustainability space were posting about how you don’t want to buy a bunch of junk that ultimately is gonna go in the trash. Their posts were getting a lot of engagement. So I thought I’d post one about how if you wouldn’t buy something for full price, don’t buy it on sale. I thought it was a good topic for fashion even if it was a bit out of my typical content. It totally flopped compared to my other posts. I’m learning to stay in my lane. Stay with what feels on brand and not doing things because someone else is doing it and it's gaining traction. You have your own voice and point of view. You can get inspiration from other people but stay true to yourself."

K: Comparison can be tough, especially on social media. But here's the key: always stay true to who you are. Remember, people are drawn to you because of your genuine perspective and voice. Embrace your uniqueness and let it shine!

What advice would you give to aspiring fashion freelancers? 

“Go for it before you feel ready! Get out of your comfort zone. Beyond that, spend time getting to know your ideal customer. What do they love? What do they want to see? And stay in that lane. Don't try to do what someone else is doing. Don't try to do everything for everybody. It comes down to your niche at the end of the day. Get really focused on what type of brand you want to reach. Get really hyper-specific. At the end of the day, talk about the brand and talk to them about their problems and their dreams, and their hopes more than you talk about yourself. This is something I teach over and over. Everybody's guilty of writing a pitch or cover letter that says I have this experience and I've done this and I can do this. There’s never anything in there that’s personalized about the brand. People send me messages about needing help freelancing. There's nothing in here about the other person. When you're asking someone for something you need to start with them and talk about them first before you talk about yourself.”

K: Great advice! I do think that one of the reasons that my freelance business is so successful is because we are so niche. We focus solely on purpose-driven swimwear and intimates. I’ve worked in this space for 14+ years so I really understand that market and I don’t want to start working on products that don’t light me up the way contour fashion does.

What's your favorite part about being a business owner? What's the hardest part?  

“My favorite part is for sure the freedom and the flexibility. I travel whenever I want. I book things on a whim. I go hiking or go to yoga whenever I want. Maybe a year and a half ago I took on a freelance client in the online business space. I thought it would be a good opportunity to learn. I got two weeks into it and I was like I can’t do this. I felt too chained and beholden. It was a decent size contract and a decent-size commitment. It was 10 hours a week ongoing. There wasn't a start and stop to a project. I didn’t want to be confined for even 10 hours a week. The difference between my business now vs. being a freelancer is that I have 100% control. I call the shots. I set the schedules. When you’re an employee you’re very much like beholden to and sort of tied to a desk. Then as a freelancer, you get a lot more freedom but you still have clients and those clients can sometimes feel like bosses. In a business like Successful Fashion Designer, I have 100% freedom. I don't even think I could go back to that freelancer level at this point."

"The hardest part is the weight on your shoulders. It’s something that I've grown immune to over the years. Everything is dependent on me. Is this the right decision? Who is there to bounce things off of? I work with various coaches to help me in my business and I have a small team. As much as I’m the leader, I still work with them very intimately. I ask for their opinion, insight, and feedback. They are very much a support network for me. But, it is hard having it all reliant on you. Luckily, I find it extremely fascinating and I love it. I love business. I love marketing. I love the psychology behind all of it. I literally could not give it up for the world.”

K: Time freedom is the ultimate luxury, right? And yes, I couldn't agree more that the weight on your shoulders can be incredibly challenging. Having a team to share ideas with has been an absolute blessing for me. They're not just my support system, they keep me sane! However, I also feel an extra level of responsibility because our design agency's success isn't just about my livelihood, it affects their livelihoods too. It's a big responsibility, but it's also an incredible opportunity to create something amazing together.

What is something you have accomplished that you are most proud of?

“Cliche, but being a mom. My son is almost four. It’s challenging in the biggest ways possible and it has made me a better person and a better business owner. I'm more efficient with my time. 80/20 really snapped into place when it came to being a mom. I would say that it is my proudest accomplishment. We also had a really hard time getting pregnant. I'm very open and transparent. I went through early menopause and I had an “undetectable” egg count. I had zero eggs so we ultimately wound up going through a donor egg and doing the whole IVF process. It was hard and challenging. I'm just really proud that my husband and I made it through that time. it was very emotionally and financially taxing. I never think about that anymore. I never thought oh my son is from a donor egg or oh my gosh we spent this much money. It’s in the rearview mirror. I'm just really proud to be a mom."

K: Thank you for sharing such a vulnerable story with me. As someone who is also struggling to bring a child into this world, it’s nice to hear that you had this experience and it was all worth the effort. I’m glad you have this opportunity to experience motherhood!!

"On the business side, I would say I feel a lot of pride in having been able to reach so many people around the world and teach them how to find their own path. Some of our students have crazy success stories and it makes me really really happy and proud to have helped to literally change their lives.”

What are the most important skills or traits you've found helpful in entrepreneurship? Are there any traits you've discovered that make it harder to succeed if you don't keep it in check?  

“Failing fast and failing often. In a small agile business, you fail a lot. We hired someone once who had come from a day job type of setting. They failed at a couple of projects and I was like okay no babe we're moving on. She was really distraught and felt like she was doing a terrible job and tried to explain that it was just a part of the routine. I've become almost immune to failing. Don't worry, I’ve had many meltdowns over failures over the years but you fail a lot and you fail fast. You learn a tremendous amount. You figure out how to do things differently and better the next time."

"A trait I've discovered that makes it harder to succeed is getting too comfortable. You kinda need to always be on your toes. It is a little bit of a constant grind. “

K: The dis-comfortzone is where all the good things happen. You’ve got to always be learning and growing to be successful in the long term, otherwise you just get stale, so I’m not surprised that your best skill to learn or adopt is failure — you learn more from failure than you ever could from pure success. 

What's your favorite 'game-changer' tool that you can share with everyone? (ie. hellobonsai, airtable, later, etc.). 

"Slack. On my team, we don’t email each other. We communicate exclusively in Slack. I love it! Also, Asana is what we use for project and task management. Those are two tools that I literally could not live without in business."

K: We love Slack on our team, too! It’s a great tool for connecting and keeping in sync with your team without inundating people with emails.

Where can we find you if we'd like to learn more about you? 

"If you would like to learn more you can find me online at Also, if you Google Sew Heidi you can find me there."

Advertisement for Freelance Accelerator Course from Heidi Weinberg


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