How to Scale Startups and Master Growth | Kat Wendelstadt | Glasp Talk #30
This is the thirty-session of Glasp Talk!
Glasp Talk delves deep into intimate interviews with luminaries from various fields, unraveling their genuine emotions, experiences, and the stories behind them.
Today's guest is Kat Wendelstadt, a dynamic marketing leader, angel investor, advisor, and mentor to many startups. Kat currently serves as the Chief Marketing Officer (CMO) at Flawless, a company at the forefront of the generative AI revolution in film. With experience as CMO for multiple successful startups, leading to a collective valuation of over a billion dollars, and being a two-time co-founder with one successful exit, Kat brings her diverse expertise to the table. As an angel investor, she has invested in over 30 startups in healthcare and AI, including notable companies like Anthropic and Pika.
In this interview, Kat shares her marketing and startup scaling journey, emphasizing her approach to connecting strategy with execution. She also dives into her investment philosophy, what she looks for in founders, and how she balances her time as a CMO, advisor, and investor. Kat provides invaluable insights into startup marketing strategies, the evolving role of AI in marketing, and how to identify and nurture meaningful innovation in emerging companies. Join us as Kat reveals her secrets to success and the future of growth in startups.
Read the summary
Glasp
Transcripts
Glasp: Hi everyone, welcome back to another episode of Glasp Talk. Today we are excited to have Kat Wendelstadt with us. So, Kat, you wear so many hats – from CMO, investor, advisor, to a mentor for many startups. Kat is currently serving as CMO at Flawless, a company leading the Gen revolution in film, and she has been CMO at multiple successful startups with a collective valuation of over a billion. She's also a two-time co-founder with one successful exit, and as an investor, she has invested in over 30 startups in healthcare, AI, and business services, including notable companies such as Anthropic, Pica, Cray, and Neuralink. It's pretty impressive! With her deep expertise in content development, B2B marketing, and early-stage startups, Kat has driven significant growth across diverse markets. Today, we will dive into her journey in marketing, her approach to scaling startups, and her insights on connecting strategy to resilient execution. Thank you for joining us today, Kat.
Kat: Thank you so much! Excited to be here.
Glasp: Thank you. So first of all, you wear so many hats – you know, you’re CMO at Flawless, a coach at System, an angel investor, and a content contributor. I’m really curious, how do you spend your day, allocate your time, and what’s your current focus these days?
Kat: My current focus is my day job as CMO at Flawless, and that’s where I dedicate the bulk of my time. It’s a normal job, so that’s what I’m focused on, and the company is going through a very exciting growth phase, so that requires quite a lot of my time. In terms of coaching, I’m a coach at a growth program called System in the UK, where they take early-stage – but not super early-stage – companies between seed and series B and help them figure out their path to growth. That’s an activity that takes place several times a year, but it’s not continuous. So you check in with your companies several times a week, but it’s not too intense. In terms of how I spend my days, I try and plan my week ahead. There's always something that gets thrown out of the window, but I plan the most important things that I have to allocate, and I’m quite focused on my focus time. Between 9 and 12 every day is essentially my time for deep work when I don’t take meetings. You can’t reach me during this time, so that way, I ensure my time is protected. I also chunk out the larger activities during my day and put them in as meetings to protect my time and allow focus.
Glasp: I see, thank you. That makes sense. And on the investor side, do you invest solo or with groups?
Kat: There are several things. As an angel investor, you have less ability to do deep due diligence than a large VC fund because you have fewer resources and less time. So the way I tend to do it is, that I have some inbound from my network – people know what I like to invest in – but I also invest with several groups and syndicates. They do part of the heavy lifting for you, so they only invest with top-tier startups and take a fee for that. So I invest through these syndicates. There’s one in the Bay Area that I work with and one in the UK called Ventures Together. They come with deals, and you decide based on your preferences where you allocate your money. I’ve done more than half my deals by myself, sourcing and vetting, but that’s not a scalable model.
Glasp: When investing, what factors are most important to you?
Kat: I only invest in what I can understand, so if I can’t understand it, I don’t invest in it – that’s number one. If it’s extremely technical and requires a high degree of understanding in an unfamiliar area, I probably won’t invest. What's most exciting to me is a team solving meaningful problems, and the earlier the company, the more important the team is. There’s a very high correlation because if you have an inspiring founder who's great at communicating, that’s a core skill. It means they can articulate the problem effectively, hire effectively, raise funding, and communicate to customers effectively. That’s as important as a specific technical skill. I look for founding teams that bring that to the table and have go-to-market advantages. You can have a great idea, but if you can’t execute it, you’re just left with an idea. It’s about how they think about go-to-market and if they have the right structure to execute. Finally, it has to be a big market, but not necessarily the biggest market. Each market is different; for instance, right now, everybody’s investing in AI, but that doesn’t mean every AI company will succeed.
Glasp: That makes sense, and communication skills are so critical. Have you seen any signs or methods to evaluate founders’ communication skills?
Kat: The pitch is the first hint. A great pitch conveys complex information in a very exciting way. You get a FOMO feeling. The simpler they can make it without losing depth is a sign of a great founder. Often, founders try to pack everything in, but you have to distill it down to basics. For an investor, each slide should hit every point an investor is already thinking about. You can get a lot from the pitch and then from interviewing them afterward. In some cases, like Anthropic, I invested due to a secondary share sale at a good rate without interviewing the founders – just knowing Anthropic is a powerful company building powerful technology.
Glasp: I see. Now, shifting to your marketing role, do you help startups with their marketing or strategy, or is it usually hands-off?
Kat: No, I’m very hands-on. I come up with a strategy that feeds off the overall business strategy, aligning marketing to help achieve overall business goals, whether that’s getting new customers, increasing brand awareness, or driving revenue. I devise plans that align with the business strategy, build systems, hire people, and even write content myself when needed. It’s a bit like founder mode in early-stage companies – you have to do a bit of everything.
Glasp: Wow, that’s really hands-on. And since you're serving as CMO at Flawless, meaning you invest in some companies but also help others. Do you have criteria for deciding to join a company versus just investing?
Kat: Yes, definitely. When I consider joining a company, I need to be genuinely excited about the problem they're solving. For example, at Flawless, we translate films across languages using software that retains the same actors, and lip-syncs and perfects the translation. So you could watch a Japanese film in English or Croatian, and it would look seamless. That excites me because it’s unlocking content on a global scale. Also, Flawless was at a stage where some marketing was in place, but it wasn’t built for scale yet. I prefer joining when I know my skill set will be most valuable, typically when they need a more structured approach and strategy for growth. I’ve done the "build everything from scratch" phase, but I prefer coming in a bit later when I can help take things to scale.
Glasp: I remember seeing a video of Flawless changing a film’s language with perfect lip-sync – it was so impressive! Does having groundbreaking technology like that make it easier to market, or does it depend on the audience?
Kat: It’s easier to market to a generalist audience when the technology is groundbreaking. For example, Flawless’ video went viral because people can easily understand the problem and the solution is visually impressive. But niche problems are equally interesting; they just need a different marketing approach. I recently spoke to someone with a medical device that helps detect skin issues. Their audience isn’t the general public but rather key opinion leaders, doctors, and practitioners. So it’s about finding the right way to reach the target audience. The product has to work and solve a valuable problem, but then we figure out the best way to communicate that value to the right people.
Glasp: Thanks, that makes sense. You mentioned preferring to join companies at a later phase. For early-stage startups, though, what would you say are essential skills or experiences for a founder or first marketer?
Kat: A founder or first marketer should be “T-shaped.” Often, the first problem is clarifying the brand and market positioning, which means starting with understanding the customer. They need to know how to interview customers, understand their jobs to be done, and map the market. The first skill is almost like being a journalist, digging deep into customer insights. Then they need to think like a businessperson, finding the most efficient way to reach that customer and communicating what the customer wants to hear, not what the company wants to say. Finally, they should be able to build scalable systems – not having to restart processes from scratch each time – and know the right tools to support their efforts. In a nutshell, it's about customer empathy, business acumen, systems thinking, and tool proficiency.
Glasp: That’s a great framework! But what about vision? Sometimes founders have a big vision, like becoming an “everything store,” but customers just want a bookstore. Have you seen that misalignment, and how do you address it?
Kat: Yes, that’s a good point! Founders often envision a massive outcome, and they want to communicate that vision to everyone. But customers care about what you can offer today. You need different messages for different audiences: sell the big vision to investors and employees but talk about the specific benefits customers want right now. A founder could have the everything-store vision but start with “We’re the best bookstore” for customers, focusing on what they can deliver today. The goal is to align each message with each audience’s needs and make sure customers can relate to what’s being offered right now.
Glasp: That’s really clear. I remember seeing a video showing executive roles and goals. Would you recommend breaking down a long-term vision in a similar way to ensure every department’s efforts align with the CEO’s goals?
Kat: Yes, but with flexibility. Things change fast, especially for startups, so we plan loosely for six months and tightly for three months. You should work backward from the long-term vision to break it down: in 10 years, we’ll be the everything store; in five, we’ll cover most categories; in three, we’ll dominate books and a second category. That way, each executive’s goals – like several partnerships or customer acquisition rates – align with that vision. In one company, we had the CEO focus on revenue, EBITA, and patient NPS, while each department had a role contributing to those metrics. Marketing drove revenue, operations maintained quality for NPS, and product-ensured new offerings. Every C-level effort needs to align with the CEO's goals to move the company forward efficiently.
Glasp: That makes sense, especially about alignment and flexibility. Sometimes there’s tension between marketing and product teams – like marketing wants acquisition, but product wants conversions. Any advice on handling that tension?
Kat: Yes, that happens often, but I think a bit of tension is actually healthy. It makes the marketing team focus on driving better-quality leads, and maybe they should share the conversion goal. Shared KPIs can help reduce that tension because both teams then work toward the same goal. For instance, marketing can be motivated to bring in quality traffic, while products can ensure the website converts those visitors. It’s about finding a balance and having some healthy push and pull to refine efforts from both sides.
Glasp: Great advice. And in terms of setting a North Star goal, any common pitfalls or tips for early-stage startups?
Kat: The biggest mistake is setting a North Star goal without understanding the customer journey and growth model. You need to know how your company grows – map it out on one page, showing how customers go from discovery to engagement to conversion. Then work backward from the ideal outcome. For a company like Spotify, “minutes listened per day” might be the North Star because it indicates they’re providing value. Draw out the path customers take to reach that outcome, then refine your goal from there. Often, the North Star is something more nuanced than just revenue, but it ultimately supports revenue growth.
Glasp: That’s insightful. In startups, things don’t always go as planned. Let’s say you set out to be a bookstore but realize most traffic is for pet food. Would you pivot or stay the course?
Kat: I’d pivot, because the primary job of a startup is not to die! If the money’s in pet food, go for it, then come back around to your original vision later. I’ve been in situations like that, where the company wanted to sell a clinical product, but most of the interest was in a wellness tool for broader audiences. It was challenging, but we realized going where the customers were would bring in revenue, enabling us to eventually develop the clinical studies we needed for the original product. You can always revisit the original vision once you have the stability and funding to do so.
Glasp: That makes sense – it's all about adapting to survive. Another topic I wanted to touch on: is AI. Everyone’s using ChatGPT, Claude, and other tools. How has AI changed how marketing teams operate?
Kat: A lot! A year and a half ago, I was just starting with ChatGPT, but now it’s impossible to do my job without it. AI streamlines workflows, content creation, data analysis, video editing, and more. I use it to transcribe customer interviews, summarize data, create content frameworks, and analyze market research. AI supports everything from brainstorming content ideas to managing Excel functions. While it hasn’t replaced human roles, it’s transformed how we work, making it faster to process information and freeing up time for more creative and strategic tasks.
Glasp: Fascinating! Do you think AI is replacing specific marketing roles or just reshaping them?
Kat: It’s reshaping them. AI isn’t good enough to replace a content person, for example, but it has changed how content is created. You can tell when something is AI-written – it’s too uniform and lacks the human element. AI is excellent for tasks like automating research, summarizing data, and supporting ideation, but a human touch is still needed to make content truly engaging and nuanced.
Glasp: That’s a great point about the human element in content. I also noticed that the tagline on your website is “Working with the world’s best companies before they’re the world’s best companies.” I really liked that! Did you come up with it?
Kat: Thank you! Actually, I worked with a fantastic copywriter who helped me with that. It’s simple but resonates with the kind of work I love – supporting companies on their journey to success.
Glasp: It’s very catchy! Speaking of companies, are there any that inspire you with their marketing, or conversely, ones you think should be avoided?
Kat: The first one that comes to mind is IKEA. They do such a great job of keeping their brand relatable and consistent, like the quirky ads about Swedish meatballs. Another classic example is the old Avis ad – “When you’re number two, you always try harder.” That honesty and simplicity make for memorable marketing. And on the more controversial side, love him or hate him, Donald Trump has a remarkable ability to stay in the public eye. It’s very strategic, and he navigates his brand incredibly well. I also like when companies are humorous and make fun of their competitors; it’s bold and memorable.
Glasp: Those are great examples! In terms of channels for early-stage startups, what would you recommend – SEO, social media, PR, or offline?
Kat: It really depends on the company and where you can get the most distribution quickly. For example, in Dr Consulta, a healthcare company in Brazil, we used outdoor media like bus shelters and subway ads. You’d think digital would be the best way to grow, but outdoor ads helped us reach a wide audience at a good price. In contrast, for a digital company like Flawless, out-of-home wouldn’t make sense. Here, we focus on PR and digital channels, showcasing the technology’s output to demonstrate value. If I had to choose just one, PR is usually the most impactful for early-stage visibility.
Glasp: PR does seem powerful. Another question, if you don’t mind – I’ve looked at your LinkedIn and your impressive career. Have you ever thought about becoming a CEO?
Kat: I have thought about it, but honestly, I don’t want that role. Being a CEO is quite lonely; you’re responsible for everything, and you have nowhere to hide. It’s especially challenging when you’re responsible for everyone’s livelihoods. I have three young children, so balancing that level of responsibility with family life is difficult enough as a CMO. Perhaps in the future, but not right now.
Glasp: That makes sense! With the rise of fractional roles like fractional CMOs or CFOs, do you think that’s a good approach for startups?
Kat: Absolutely. Fractional roles work well, especially for marketing, where CMOs often have the shortest tenure. Marketing can be seen as subjective, and since everyone has an opinion on it, it’s often the first area to change. Fractional roles allow companies to bring in expertise to solve specific problems without the risk of a long-term hire. It’s similar to hiring a freelancer or contractor but with a deeper commitment and alignment with company goals. It reduces the risk on both sides and brings in experienced people who know how to achieve specific outcomes efficiently.
Glasp: I hadn’t thought of it that way – that makes a lot of sense! This is a bit of a random question, but in marketing interviews, what do you look for in candidates? How do you gauge if someone is a good fit?
Kat: First, I look for cultural fit. They need to be high performers but also genuinely nice people – no egos or difficult personalities because one person can impact the whole team. Then, I’m interested in their experience, but even more in their ability to learn and problem-solve. Especially in startups, you need people who are hungry, resourceful, and willing to hustle. It’s not just about skill; it’s about the drive to find creative solutions and not just rely on easy answers.
Glasp: I saw your post on LinkedIn about hustle – that resonated! For our audience, which includes aspiring product managers, marketers, and researchers, do you have any advice on excelling in their roles?
Kat: My two main pieces of advice are to read constantly and network. You have to dominate your field of knowledge, so keep reading and learning. I read marketing blogs daily and am always staying updated. Networking is equally important – you need to get out, meet people, go to events, reach out to folks in your industry, and nurture those connections. Technology can’t replace relationships, and networking opens doors to opportunities, inspiration, and knowledge sharing.
Glasp: Great advice! Do you have any favorite books or go-to resources for learning?
Kat: Yes, for marketing, I highly recommend Traction – it’s a bit older but still relevant. For management, High Output Management by Andy Grove is the best book ever written. I also follow three people whose content I think is the best out there: Emily Kramer from MKT1, Elena Verna, and Katelyn Bourgoin. I subscribe to all three because they’re practical, insightful, and always add value to my work. Their content keeps me at the forefront of the field.
Glasp: That’s great – I’ll look into those names! What makes you feel that they’re exceptional?
Kat: They offer constant value. Their content is easy to read, practical, and solves real problems with frameworks and examples. I use it to educate my team, share insights with management, and stay ahead in my field. It’s worth the investment because it’s always relevant, timely, and actionable.
Glasp: Thank you for sharing all these insights. Last question – since Glasp is all about sharing what we’re learning and leaving a digital legacy, we’d love to know: what legacy or impact would you like to leave behind?
Kat: I love that question! I think about what’s essential at the base level – the things that allow everything else to flourish, like health, environment, education, and supporting women. With my investment work, my hope is that anything I don’t need by the end of my life can go toward causes that support these areas. I’m involved with one organization that just won the Goldman Prize for the Environment. They protect indigenous lands in the Ecuadorian rainforest, and I helped build schools that preserve traditional knowledge and provide education for women and children. It’s a project close to my heart and aligns with the legacy I hope to leave.
Glasp: That’s incredibly inspiring, Kat. Thank you so much for sharing your journey, insights, and wisdom with us today. It’s been a pleasure having you on Glasp Talk.
Kat: Thank you so much – I really enjoyed the conversation. Great questions and I’m so pleased to be here. Thank you!
Glasp: Thank you!
