$8K/Month – Creating high-end, eco-friendly wooden surfboards – David Dennis of Ventana Surfboards and Supplies

INTERVIEW VIDEO (Length – 44:14)


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David Dennis of Ventana Surfboards and Supplies shares the story of creating a high-end, beautifully designed, and eco-friendly wooden surfboards that sell for thousands of dollars and can be used as art-pieces.

Episode Summary

David Dennis of Ventana Surfboards and Supplies,” host Sushant interviews David Dennis, co-founder of Ventana Surfboards and Supplies. David started the business nine years ago with his partner Martine Stipout, a wooden surfboard shaper and amazing woodworker. Ventana focuses on sustainability and creating high-end, eco-friendly surfboards and products, ranging from affordable items to expensive performance art pieces. David handles sales, marketing, and business development while Martine builds the surfboards from reclaimed wood. Though most sales still come from in-person events, Ventana has expanded into apparel lines and collaborations with designers to reach a wider audience. David utilizes Microsoft tools for content creation, but emphasizes the importance of human touch and original ideas. Throughout his journey, David has learned the importance of testing products, minimizing risks, and maintaining ownership in his business. Ventana Surfboards and Ventana Surf can be found on various social media platforms

  • 00:00:00 In this section of TrepTalks, host Sushant welcomes David Dennis, co-founder of Ventana Surfboards and Supplies. David, who previously worked at Microsoft, started the business nine years ago as a sideline project. He was inspired by his partner Martine Stipout, a wooden surfboard shaper and amazing woodworker, whom he met while photographing an exhibit for a nonprofit. Together, they built Ventana with a focus on sustainability and creating “performance works of art” that combine craftsmanship and adventure. While the surfboards are priced from $1,000 to $20,000, the business offers various environmental-friendly products, ranging from a $5 bar of wax to $115,000 surfboards. David, who handles sales, marketing, and business development, brought the sustainability perspective to the brand, working alongside Martine, who focuses on building the surfboards from reclaimed wood. Over time, these surfboards not only perform well in the waves but also appreciate in value, appealing to a global market
  • 00:05:00 In this section of the YouTube video titled “David Dennis of Ventana Surfboards and Supplies”, the speaker discusses the unique value proposition of their business, which combines artisanship and the stories behind the sustainably sourced materials used to create high-end surfboards. The boards, which can fetch significant prices, are primarily bought by high net worth individuals and corporations. To make the brand more accessible to a wider audience, Ventana has also created an apparel line, collaborations with designers, and other product offerings, all based on the aesthetic of the surfboards. The products are not mass-produced; instead, they work with partners who donate materials, giving them free publicity and expanding their reach. The majority of their sales still come from in-person events where they can engage with customers face-to-face. Their e-commerce business largely consists of smaller items, and while it’s growing, it’s not yet a massive juggernaut
  • 00:10:00 In this section of the YouTube video titled “David Dennis of Ventana Surfboards and Supplies”, the founder of the company discusses their unique business model focusing on sustainability and upcycling. They use salvaged materials to create various handmade items, from pens to bottle openers, and even surfboards. Ventana also sells their products across multiple platforms including Shopify, Etsy, and Facebook, with the most success coming from face-to-face events. The business was founded on a commitment to ocean conservation, which led them to donate at least 5% of their revenues to relevant organizations and establish a scholarship for students studying ocean conservation. While there is limited scalability in the handcrafted surfboards, they envision growing the business through apparel and accessories that align with their brand, and potentially opening a retail space in the future
  • 00:15:00 In this section of the YouTube video interview with David Dennis of Ventana Surfboards and Supplies, Dennis discusses the challenges they faced with wholesale business and why they shifted their focus to direct-to-consumer sales. They discovered that the workload and logistical issues associated with wholesale, particularly with ensuring sustainability, weren’t worth the smaller margins. Additionally, they found that their customer base extended beyond just surfers, as people worldwide appreciate the connection to the surfing culture and ocean, regardless of their geographical location. Dennis also mentions their experimentations with AI technology in various aspects of their business, such as blog post writing, model design for product pages, and creating a thousand-piece puzzle, but have decided against using AI to design surfboards as of now
  • 00:20:00 In this section of the YouTube video titled “David Dennis of Ventana Surfboards and Supplies”, the speaker, David, discusses his dual role as an employee at Microsoft and the founder of Ventana. He explains how his work at Microsoft, particularly in the ads business and small business strategy, is informed by his experiences at Ventana. Furthermore, he shares how he uses various AI tools from Microsoft, such as ChatGPT and mid-Journey, to create content for Ventana and enhance his work. Though AI tools can create drafts, David emphasizes the importance of editing and refining the content to ensure a human touch
  • 00:25:00 In this section, the speaker shares an innovative use case of incorporating Microsoft Teams with chat GPT for content creation. He explains how he utilized this technology to transcribe an interview with a local Santa Cruz figure, generate an initial draft of an article using AI-generated notes, and then edit it for publication. This method saved time, making the writing of the article faster, but required significant editing for the final product. The speaker also discusses the potential future of AI in content creation, suggesting it may become as good as human-written content, and raising the value of original content and ideas. He questions the possibility of search engines penalizing AI-generated content and explores potential business models where search engines pay for original content. Additionally, he shares his perspective on AI’s potential impact on search engines and disrupting search advertising, emphasizing the importance of original content
  • 00:30:00 In this section of the YouTube video titled “David Dennis of Ventana Surfboards and Supplies,” David discusses the importance of original content and experiences that are human and real in a world where AI is increasingly used to create music and other forms of media. He believes that as AI becomes more prevalent, live music and experiences that are authentic will become even more valuable. David also shares his entrepreneurial journey and the lessons he’s learned while running Ventana, including the importance of testing products on a small scale before investing heavily and avoiding the assumption that a product will be successful without doing the necessary research and iteration. He emphasizes the importance of not believing one’s own marketing and taking a measured approach to entrepreneurship
  • 00:35:00 In this section of the YouTube video interview with David Dennis of Ventana Surfboards and Supplies, he reflects on his business experiences and shares some insights. He acknowledges the importance of continuing to work while running a business to minimize risks, and the need to let go of control and bring on more team members for growth. Dennis mentions that most of his e-commerce sales are from events and fulfillment is often done directly to customers. He recommends The Lean Startup for entrepreneurs, expresses excitement about the potential of AI in e-commerce, and speaks highly of Patagonia’s business model and sustainability efforts. He cites his father, an early software entrepreneur, as a role model and shares the advice: “Don’t take investment if you don’t need it
  • 00:40:00 In this section of the YouTube video titled “David Dennis of Ventana Surfboards and Supplies,” the interviewee, David, shares the advice he received from a mentor named Clop about entrepreneurship and business ownership. Clop suggested that if entrepreneurs can grow their businesses independently and keep control without taking on investments, they won’t have to answer to others. While scaling may require external funding, David emphasizes the importance of ownership for entrepreneurs who aim to reap the rewards of their efforts. Ventana Surfboards and Ventana Surf can be checked out on various social media platforms

People & Resources Mentioned in the Episode

Book: The Lean Startup by Eric Ries

What You’ll Learn

Interview with David Dennis of Ventana Surfboards and Supplies

[00:00:00] Introduction to TrepTalks
[00:00:15] Welcoming David Dennis, Co-founder of Ventana Surfboards
[00:01:19] Origins of Ventana: Sustainability and Entrepreneurial Journey
[00:02:19] Ventana’s Unique Business: Surfboards as Art and Sustainability
[00:03:26] Collaboration: Craftsmanship and Sustainability Angle
[00:04:57] Board’s Value and Clientele: The Unique Market
[00:07:31] Production and Marketing Strategy: Collaborations and Outreach
[00:08:57] E-commerce Expansion and Handmade Product Line
[00:12:11] Sustainability Focus and Eco Apparel
[00:13:00] Ventana’s Commitment to Sustainability Efforts
[00:14:00] Business Model and Future Goals
[00:15:00] Scalability and Retail Expansion
[00:16:00] Target Market Diversity: Beyond Surfers
[00:17:00] Surfer and Ocean Lover Appeal
[00:18:00] AI Integration in Ventana’s Operations
[00:20:00] Microsoft’s Influence on Ventana’s Approach
[00:22:46] AI in Content Creation
[00:23:40] AI: Enhancing Work, Not Replacing Creativity
[00:24:48] AI’s Role in Draft Generation and Iteration
[00:25:37] AI Integration with Transcription and Writing
[00:27:15] AI’s Impact on Search and Original Content
[00:28:07] Microsoft’s AI Investment and Future Predictions
[00:31:00] Balancing Entrepreneurship and Full-Time Work
[00:32:48] Learning from Setbacks and Entrepreneurial Mistakes
[00:35:46] Ventana Surfboards Operations and Team
[00:36:58] Rapid Fire Round: Book Recommendation for Entrepreneurs
[00:37:29] Exciting Innovation in E-commerce and AI’s Role
[00:37:59] Productivity Tools and AI for Enhanced Efficiency
[00:38:38] Recognizing Patagonia’s E-commerce Model
[00:39:00] Inspirational Entrepreneurial Figure: David’s Dad
[00:39:40] Valuable Business Advice: Avoid Unnecessary Investment
[00:40:38] How to Connect with Ventana Surfboards

Rapid Fire

In this segment, the guest will answer a few questions quickly in one or two sentences.

David Dennis of Ventana Surfboards and Supplies

  1. Book recommendation that you would make to entrepreneurs or business professionals (Response: The Lean Startup by Eric Ries)
  2. An innovative product or idea in the current e-commerce retail or tech landscape that you feel excited about (Response: Artificial Intelligence)
  3. A business or productivity tool or software that you would recommend/Productivity Tip. (Response:)
  4. A startup or business (in ecommerce, retail, or tech) that you think is currently doing great things. (Response: Patagonia)
  5. A peer entrepreneur or businessperson whom you look up to or someone who inspires you (Response: His father who started his first software company in 1972)
  6. One networking tip or building and sustaining valuable professional relationships.
  7. Best business advice you ever received (Response: If you don’t have to take investment, don’t)

Interview Transcript

Sushant Misra of TrepTalks: [00:00:00] Hey there entrepreneurs. My name is Sushant and welcome to Treptalks. This is a show where I interview successful e-commerce entrepreneurs, business executives, and thought leaders and ask them questions about their business story and also dive deep into some of the strategies and tactics that they have used to start and grow their businesses.

And today I’m really excited to welcome David Dennis to the show. David is the co-founder of Ventana Surfboards and Supplies. Ventana creates wooden surfboards that are pieces of art and that also perform well in the waves. They have also created a line of apparel and surf supplies that match the boards and that fit with their brand values, which are craftsmanship, responsibility, and adventure.

And today I’m going to ask David a few questions about his entrepreneur journey. And some of the strategies and tactics that he has used to start and grow his business. So, David, thank you so much for joining me today at Triptalks, really, really appreciate your time. Thanks for inviting me. Awesome. So, definitely a cool background and we were just discussing, um, you know, what you [00:01:00] do and you work at Microsoft and this is kind of your, um, side hustle or business project.

So, can you share a little bit about your business, your background? When did you start this business? How did you get the idea? And, um, what really motivated you to get

David Dennis Ventana Surfboards and Supplies: into entrepreneurship? Yeah. So we started Ventana, uh, my partner and I together as a, as a corporation, um, over nine years ago. And it started because I do photo exhibits for nonprofits to raise money for their organizations and Microsoft supports those through our matching program.

And one of the exhibits that I photographed was of surfboard shapers in and around the Santa Cruz area. And one of the people I photograph was my business partner now, who’s named Martijn Stipoud, who’s one of the most amazing woodworkers and surfboard builders in the world. And I loved what he was doing.

I had an idea for an eco surf company. He was already building these incredible wooden surfboards. So [00:02:00] we decided to start a business together to try and showcase what’s possible in the world of sustainability in the context of the surf industry.

Sushant Misra of TrepTalks: And so how do you describe your business? I mean, these surfboards, obviously, you know, the way they’re described are they’re pieces of art and of course, you know, the price point is.

You know, uh, I mean, anywhere between, uh, what I see on your website is from 1, 000 to 20, 000. Yeah, I

David Dennis Ventana Surfboards and Supplies: mean, our wooden surfboards are 10, 000 to 15, 000. So we have products that are lower price, like we sell a bar of wax that’s 5 all the way up to a 15, 000 surfboard. You may be looking on the website at our art pieces, which are smaller versions of the boards that hang on the walls that aren’t meant for surfing.

Um, but. You got it right. Our surfboards are what we call performance works of art. They’re always built to surf, and while not all of them surf, all of them do stay inside and hang on walls because they are pieces of art and they have [00:03:00] amazing backstories. The woods that we use have these incredible stories behind them.

So, they are often used for interior design projects or corporations will sometimes buy them for offices or stores. But they are always built to surf. We surf ours. We love ours. You can see one of, uh, one of ours in the background here. Uh, they’re, they’re a real blast to surf, but Basically, the company is focused on sustainability and products at every price point.

Yeah, I mean, the surfboards

Sushant Misra of TrepTalks: look really, really beautiful. I have to say that. Um, and would make great decoration pieces at home or, you know, as you said, office and so forth. So really, so your partner was kind of the, the, uh, the craftsman behind this. And you kind of brought the sustainability angle to this and, um, uh, So it, so it creates more value to, to different, um, people?

David Dennis Ventana Surfboards and Supplies: Um, yeah, I would say so. I bring sales, marketing and business development, e-commerce, web development, [00:04:00] that sort of stuff. He’s the builder. He was building these boards in part because it was less expensive out of, um, salvaged wood redwood floorboards in the 18 hundreds and old fences and things like that.

So he was doing something in the sustainability space. I wanted to do more. To expand the brand in a sustainable direction. But basically I’m not allowed to touch the tools. He’s the artisan and I’m the sales and marketing side of the business, which I love. And, uh,

Sushant Misra of TrepTalks: I mean, I’m assuming that, you know, from a market perspective, this is, this is, these are pieces of art.

So, um, and somewhere I also read that, you know, they kind of appreciate and value over time. Can you talk a little bit about, I mean, what was the business that Martin was Previously, and, um, what is really the, um, the market like who’s who’s buying, um, these kind of,

David Dennis Ventana Surfboards and Supplies: uh, boards. Yeah, Martin was building [00:05:00] surfboards before wooden surfboards at a bit of a lower price point.

The thing that I offered was a perspective on how we might be able to add more value to the boards, especially around telling stories around the materials. So his artisanship has gotten better and better and better every year. I mean, he’s amazing. But one of the things that I thought we could do better was telling our story around.

The importance of sustainability, but also the materials. So as an example, we have wood from the hull of the boat that John Steinbeck sailed into the sea of Cortez in 1940. We have wood from old houses. We have salvaged wood from really historic buildings. We have Um, you know, stair railings from an old hotel in New York.

We have just an incredible materials. And so what makes the boards unique is both the artisanship and the stories behind the materials that are in them. And so, uh, Martine had been building surfboards. When I got involved, we came up with a strategy to increase the [00:06:00] value of those boards and yeah, they have gone up over time.

Oftentimes, if someone wants to sell a board, one of our boards used, they can get, not always, but they can get often get more than they paid for it because they are rare. Most of it, as you can imagine for the surfboard specifically, it’s generally high net worth individuals, you know, maybe have a second home, a beach home.

Um, we’ve done a lot of with corporate, um, cut customers, um, lucky brand Plantronics, Starbucks, a few others that we’re not allowed to name. Um, but, uh, but then what we, what we often do. People love what we’re doing with the surfboards, but obviously not everybody can afford a 10 or 15, 000 surfboard. So we’ve created an apparel line.

We work with designers all over the world to create, you know, sustainable clothing with designs that match the surfboards. And we’ve got surf wax, and we You. We create other art pieces. We’ve invented some products. Um, we do, you know, all kinds of really interesting collaborations that are all based on the aesthetic of the [00:07:00] surfboards.

Um, because we want everyone to be able to access the brand, even if they can’t pay for a 15, 000 surfboard. Someday, maybe, but you know, not everyone’s going to do that for sure.

Sushant Misra of TrepTalks: Uh, so are these products made to order or, um, so you go out, you do sales and marketing, you bring new orders. And then based on that, these are, so can you share like how many boards are you generally producing in a year and, um, how do you kind of pitch them to, to your clients?

David Dennis Ventana Surfboards and Supplies: Yeah, so if we’re just talking about the surfboards and not the apparel or some of the other products we’ve created, just focused on the surfboards, um, we’re only doing about 10 or 12 a year. And a lot of what we’ve done to get our story out is collaboration with other businesses. So we’ve got, as an example, we have 30 or 35 different partners who give us wood.

It’s interesting. We’re a wooden surfboard company, but we don’t buy wood. We have a rule that we’ll try to never buy wood. Okay. Because that keeps us. That sort of [00:08:00] keeps us honest in terms of sustainability. So, uh, we work with companies that want to donate things to us. And as we’ve gotten more and more publicity around this, we’ve done TV and podcasts and radio and things.

People realize that if they give us materials, we’re going to amplify their message. So we do a lot on social media. We do a lot of, you know, as, as we’re talking, I’ll be talking about some of the companies we work with. And so they’ll basically be getting free publicity for their trash. And so that’s one way we get the story out because they then promote what we’re doing on their social media and in their.

Marketing and that helps us expand our reach on. Then we’ve just built up a really good following over the years through events through social media. A lot of our business just comes in from people finding us on LinkedIn or Instagram or other places like that.

Sushant Misra of TrepTalks: And, and the other product lines, your, um, eco apparel, surf supplies, the smaller items.

I mean, that’s really kind of the, the, um, [00:09:00] the e commerce business that you have. Can you talk a

David Dennis Ventana Surfboards and Supplies: little bit? Yeah. Sure. Yeah. We do sell surfboards online. Like it’s not uncommon for somebody to just find us through Instagram and buy a 12, 000 surfboard on the, on the website. It doesn’t happen that often, but it’s happened a bunch.

But, um, but yeah, I mean, most of our e commerce business is sort of the other products, the smaller things. Um, and that’s a pretty good business. Most of what we do is an events online when we’re able to tell the story one on one, like at a craft fair or an art and wine festival or something like that. Um, When we’re engaging face to face with customers, our sales are fairly sizable.

Um, our e commerce business is growing, but it’s not, it’s not, you know, some massive juggernaut that’s, you know, competing with some of the major brands. Yeah, it could be at some point. Um, but yeah, if you go through, one of the things you’ll find in our site is we try to use everything. Right. So we’re taking [00:10:00] salvaged materials and woods and other, not just wood, but, and we’re creating things out of them.

And then whatever’s left over, we try to create things out of that as well. So it’s, it’s literally salvaged on top of salvaged on top of salvaged as an example. Um, we’ll make pens. So my partner will make pens out of wood that are from the wood that’s left over from the surfboards or bookmarks or knife handles or other items that are book bottle openers.

So we’re literally trying to use every scrap of every wood. Um, and then we can tell a really cool story at different price points for different customers, which we then can promote online or in person at our events.

Sushant Misra of TrepTalks: So that’s really interesting. Like all of these products are kind of handmade. Uh, they’re not like mass produced.

Okay. That’s, that’s awesome. Um, so you, your main channel is really your website or are you selling, because you know, these kinds of handmade items I would assume would do well on a platform like Etsy. Are you also selling on, um, any of these marketplaces? [00:11:00] We

David Dennis Ventana Surfboards and Supplies: do, we do have an Etsy store, but we’ve, I’m actually just this week starting to do more with Etsy, although they have some odd.

Thing right now, some bug that’s keeping us out of the store because of some tax issue that they’re not understanding. But anyway, yeah, we built out Etsy. We basically, what we do is we’re on Shopify and we’ve got almost every selling platform integrated into Shopify with the exception of Amazon. Um, where, you know, you can buy on Tik TOK, you can buy an Instagram, you can buy on Facebook, you can buy.

Uh, across the internet with all of the different services that integrate with Shopify. Shopify is great in that. You know, you’ve got your product catalog and you can fan it out to Google and being in all the other places I mentioned and allow the purchasing to happen there. Um, we’ve done a little bit on Etsy, you know, a little bit here and there on eBay.

Um, but most of the time it’s Shopify, um, with the tentacles out into the world. And some we’re now experimenting with some online advertising, which we haven’t done a lot of, but again, like. The place where we have the biggest success is old [00:12:00] school face to face events. We don’t have our own retail store.

I just don’t have time for that with my day job. But our events are really, really successful. So we try to do a few of those a year. So you kind of

Sushant Misra of TrepTalks: got into this business really because of the focus on sustainability, right? So, um, you know, you have this eco apparel line and so forth. Can you talk about your sustainability efforts?

And, um, I believe I read somewhere you kind of donate 5 percent of your revenues or profits and things like that. Uh, what, what are all the things that you’re doing around sustainability? Yeah. So

David Dennis Ventana Surfboards and Supplies: for me, I grew up, um, in a family that was, you know, very focused on animal, animal and environmental conservation, but I started surfing late in life when I was 40 and I got really, really into it.

And so I also at the same time got passionate about making sure the oceans were protected. Cause if you don’t have a healthy ocean, you can’t go surfing. And around that time, I did a photo exhibit for the surf rider foundation, focused on surfboard shapers. I met my partner [00:13:00] and I decided that we could do better than the industry.

In terms of sustainability. So we like to talk about how we basically built a company on trash. And so, and we collaborate with other companies that have similar brand values that we have. And then in addition to that, we donate 5%, at least 5 percent of our profits to ocean conservation organizations. And last year we set up what we call the Ventana ocean conservation scholarship.

So we also donate money to our own scholarship, and then we, um, we award the scholarship to a university student that’s studying ocean conservation, uh, and we just, uh, we just gave our first, uh, 3, 500 award a couple of months ago, and we’ll do it again this coming year. So we’re not just about creating products that are sustainable and showcasing what’s possible with trash.

But also, um, donating money to organizations and people that we think are doing good work. What is your,

Sushant Misra of TrepTalks: I mean, what do you think about your business model? [00:14:00] Um, and how do you see it? Like, what is your kind of like future goal with this? Like, I mean, this is a part time project for you right now. But, um, is there any scalability in, uh, in, in what you’re doing right

David Dennis Ventana Surfboards and Supplies: now?

There’s not really scalability in the surfboards. The surfboards will always be handcrafted artisan performance works of art that are maybe 10 or 12 a year. What we think we can grow, and maybe, you know, as I at some point retire from Microsoft and want to put more time in this, I can envision us growing the brand.

Where we’ve got, you know, apparel that matches the aesthetic of what we’re doing and growing the apparel business, um, and growing some of the accessories, uh, because we think that can scale. Uh, and we’re, we always want to be true to the core of the surf brand and these amazing artists and surfboards. Um, but I, I think, you know, I can envision us Opening retail at some point and potentially growing a wholesale business where we [00:15:00] expand the apparel line.


Sushant Misra of TrepTalks: I mean wholesale you can still do like online with a platform like fair. Um, have you have you considered? Um, or are you already on that platform? No,

David Dennis Ventana Surfboards and Supplies: we’re not We so we we’ve done some stuff early on with brand boom, you know, which was a shopify the problem that we found with wholesale was it’s a heck of a lot more work than I expected, uh, and You know, in part because we have a really high bar for sustainability that we don’t want to outsource like drop shipping and, you know, real time creation of T shirts and things like that, because oftentimes they’re wrapped in plastic and we don’t have control over the packaging and it becomes kind of a logistical problem for us to keep our artists and our eco friendly bar where it needs to be.

The other problem with wholesalers, the margins aren’t as good. Um, we found that we were working with several surf shops that didn’t pay their bills on time and we were essentially loaning the money Constantly having to try and get our you know [00:16:00] payments There are return to vendor issues where they decide they don’t like something or it’s not quite selling as fast as they had hoped And then they want to return it And it’s just a hassle.

So if we were going to do wholesale, we’d have to address some of those issues Um, I think direct to consumer is probably the better direction for us longer term So

Sushant Misra of TrepTalks: your surfboards are kind of like targeted towards more of heightened network individuals or businesses that kind of want to decorate their, um, their places and add kind of the sustainability, uh, element to, uh, to their brand.

Um, but I think your, um, other products, which are, you know, lower, uh, Price. Do you, uh, is your target market really the people who are in the surfing, um, sport? Uh, like do they kind of resonate more with your products or is it kind of just any, anyone out there who likes, uh, you know, handmade, uh, uh, [00:17:00] products, uh, you know, collectibles and things like that.

David Dennis Ventana Surfboards and Supplies: It’s the, it’s the latter. So one of the things that’s interesting is you find, you know, some of the larger surf brands, um, O’Neill and Rip Curl and Quicksilver. I mean, they sell all kinds of apparel and products to the, you know, the middle of the United States where there’s, or elsewhere in the world where there’s no ocean, because everybody wants to be associated with, you know, the surfing culture and ocean and things like that.

And so, you know, we sell our shirts, uh, all over the place. Um, And all over the world, actually, even if they may be sort of surf themed, they, you know, sometimes we’ll showcase animals from our region, um, you know, whales, dolphins, things like that. Everybody loves the ocean. And so, uh, it’s not just surfers.

And I think that’s important for our growth because you know, surfing is amazing, but if you’re only targeting surfers with your products, you can’t, you can’t really scale. [00:18:00] That’s a small market.

Sushant Misra of TrepTalks: Okay. Um, are you, uh, is there any value that you bring? From your work at Microsoft, I know Microsoft is doing a lot of things around AI these days.

Yeah, for sure. Is there any, um, are you doing anything that involves any technologies using AI in your business and things like


David Dennis Ventana Surfboards and Supplies: Yeah, so I could probably talk about this one for hours, but we’re doing a lot of experimentation in Ventana. I am with AI. Uh, blog post writing. I do a lot of editing. Um, we’ve used it for inspiration.

Some of our models that we’re using because we can’t really afford models. Um, uh, in our, on our product pages are AI generated. Um, we, I actually wrote a blog post on our website. Uh, around whether we should use a I more, you know, because we’ve got this handcrafted artists and brand and the surfboards, you know, are essentially thought up by my business partner.[00:19:00]

And so, you know, one of the questions we put out there, as I said, I put out a bunch of a I imagery and said, here’s a surfboard we can create. That’s based on, you know, an AI generated image. Should we be doing that? Like, does that fit with a brand that’s, you know, focused on artisanship or are we sort of, sort of cheating in some way?

And the feedback was mixed. And we decided that for now, we’re not going to use AI to design surfboard, you know, create surfboard designs, but I am using it in other ways. As an example, we’ve just launched a puzzle, a thousand piece puzzle for the holidays and the image, the core image of the puzzle was generated by AI.

Uh, and then I did a lot of Photoshop editing to add our surfboards to it and whatnot, but Ventana surfboards. com slash puzzle. You can see the image that was generated by AI. Whoa. And so that, that’s, that’s one of the things and, and I could go through other examples of how I’m experimenting with AI in different ways for content.

The other thing is back the other way. So I work at Microsoft, [00:20:00] I’ve been there for over 22 years. I work on the Outlook email team and we’re making tremendous investments in ai. And as you can imagine, much of the work that I’m doing in Ventana with AI is using Microsoft tools, or at least tools that were, you know, where we invested in chat GPT and using some of their technology that’s integrated.

Into products like Bing and Microsoft Word and PowerPoint and things. So. So that’s on that side, but a lot of what I do at Microsoft is also informed by Ventana as an example, uh, I was responsible for, um, part of the ads business within Outlook and Skype for a while. And so I was experimenting with different ad platforms using Ventana to do it.

So I could learn about. Some of the ad experiences that we were looking at building into our products. I worked for a while on our small business strategy for Outlook, and that was very large, largely informed by my experiences as a small business and working with other small businesses. And so Microsoft, the folks that I work [00:21:00] with are fine with me, you know, working on Ventana on the side, because it’s helping me use our tools and learn about them and give feedback, but also informing some of the work that we do in Microsoft, because I have this direct small business background.

Well, that’s, that’s very

Sushant Misra of TrepTalks: nice. And, uh, I’m looking at the puzzle page, um, and the image, it’s beautiful. I mean, how did you put your surfboards in that image? Like, did you, how do you integrate

David Dennis Ventana Surfboards and Supplies: that? Yeah. So this would be another hour long conversation, but the, so it looks like just, you know, a standard AI, uh, image, but there’s actually a few different tools that I used.

And I’ll just give you a quick summary. Um, the initial image was generated by mid journey, which is not a Microsoft technology, but it’s a terrific, you know, image generator. And basically what I said was create, I think I said, create a surf shop in a Redwood tree. And that’s what it came up with. It looked more like a treehouse to me, and we have this character we’ve created called the Ventana Surf Squatch.

The original design was actually done [00:22:00] by hand by an artist in Brazil that we work with. And the Ventana Surf Squatch is this, is this Bigfoot, this Sasquatch that surfs. And so we have t shirts and stickers, and we’ve created all this, this legend around this Surf Squatch. So to me it looked like a, a, a house that a Surf Squatch might live.

So then I use mid journey to generate a surf squatch. I edited in the surfboard with Photoshop. So if you look in the bottom right side, I think of that image, you can see the big foot, the surf squat. And then all the other surfboards, I basically used another tool called PhotoRoom to remove the background of some of our photos, and then I used Photoshop to integrate them into the image.

So, it’s a lot of work to create that, even though elements of it were created by AI, in different tools of AI.

Sushant Misra of TrepTalks: No, it’s beautiful. And I think it would make, uh, definitely creates a great, great puzzle for sure. I mean, I have been, even last evening I was playing with different AI, just doing research, just trying to create a [00:23:00] blog post.

Um, because, you know, of course I’m creating all this content with people and, uh, you know, which can be converted into blog posts that, that has value and, you know, maybe SEO optimized. Um, Thank you. That’s right. I think on its own, uh, I mean, I’ve been experimenting. I think that, you know, what, what my experience has been is you have to give more direction.

So you can’t just say, you know, take, you know, go look at this URL and based on the content there, create a blog post. You can clearly tell that’s not human written. You have to provide more structure. I mean, what have you been doing in terms of content creation with AI and what has been your

David Dennis Ventana Surfboards and Supplies: experience?

Yeah. I mean, I look at it as a performance enhancer, like it enhances, accelerates my ability to, to do work, but it’s not, you know, if all I did was write, write a blog post on sustainability and surfboards and then just copy and pasted it, it would be very kind of. [00:24:00] It would be obviously AI, I think, and it would be fairly generic.

Now I might want to do that because it’ll help me with that search engine optimization or something like that. But I think one thing people forget about AI is that most of these tools are, it’s chat, it’s a conversation. Yep. Right. So I might say, write a blog post about sustainability and surfing, and then it comes back with something and I’ll say, okay, rewrite it, but make it shorter and incorporate the concept of hollow wooden surfboards from Ventana into the blog post.

And I would, I’ll just keep iterating until I get a core that I like, and then I’ll edit the heck out of that. So it’s, it’s helped me, um, get started, but it’s not. It’s not, you know, I guess in some context, you know, there might be a reason why you just copy and paste it somewhere. But, um, but I don’t do that.

I use it. I chat a lot. I use it as a, as a way to generate drafts. I’ll give you a really interesting use case that I, um, that I used it for recently. [00:25:00] Uh, and it was, I incorporated, um, Microsoft Teams with, um, with ChatGPT or chat. bing. com, which is Microsoft’s, um, one of Microsoft’s iterations of ChatGPT are built on top of it.

Um, I, I write a quarterly article for a magazine called Santa Cruz Vibes, and I, the one that just came out this week was an interview with somebody similar to what you and I are doing. And I interviewed the person in Teams, Microsoft Teams. Teams has transcription capabilities, as many of these tools do.

But it also provides a recap and an AI generated summary of the conversation. So it’s like, it’s not just the transcript, but it’s automated notes. And so what I did with this, with this interview with this gentleman, a guy named Matt Swinnerton, who runs a great organization called Event Santa Cruz, I interviewed him, [00:26:00] transcribed it, used the AI generated notes from the conversation, put it in the chat GPT.

And I said, take this inner, these interview notes and write an article about it for a magazine. Hmm. And the magazine’s targeting local people in Santa Cruz as well as tourists, and it came out with a pretty darn good initial draft of an article with some structure that I could work with. Now, I spent hours editing that.

But it was a really interesting way to take the transcription of an interview, turn it into the use AI, two different AI tools, essentially to turn it into the foundation that I could then work with. It just made the writing of the article faster. So I don’t think it’s cheating. It wasn’t plagiarism. It just was a way to accelerate the creation of the article that ultimately was my work because it was my questions.

There was the responses of the subject. It was my editing. Um, it just helped.

Sushant Misra of TrepTalks: Exactly. I think that’s what I [00:27:00] find. It helps you to get started, but then you, there is, you have to spend some time editing and just making, making it your own. I mean, you’re working at Microsoft, and I’m assuming Microsoft is making a lot of investment towards AI and things like that.

Um, what do you see as the future? I mean, um, for content creation, let’s say for example, right? I mean, I’m assuming that five years down the road, what we are considering now is, you know, uh, something that can help you get started will probably be as good as human or, you know, kind of approaching there in terms of writing articles and things like that.

Um, would search engines be penalizing that or be able to detect that content and penalize it? And I’m assuming that Then the value of like original content and original ideas that don’t exist on the internet, they’ll, they’ll be like a lot more valuable. And even maybe there’s a business model there where [00:28:00] search engines pay people to create original content or something like that.

I mean, what, how do you see it given that you’re working at, uh, Microsoft? I don’t,

David Dennis Ventana Surfboards and Supplies: I don’t know. Um, and any answer I’m gonna give right here is not me talking as a Microsoft employee. It’s just, you know, perspective. I’m finding that I’m using ai. As a search engine, as much as I’m using it to create content as an example, when you and I were trying to get the other tool we were going to use for this interview, instead of going to a search engine or trying to find the help menu in the tool to figure out how we could create a back.

I could add a background. I just went to being chat in edge. Which is there’s a sidebar and edge that’s you can click a button and just chat with on the side of it, but Microsoft edge. And I just asked the question because I knew that I, you know, the large language model had ingested all the Internet with being on top of it.

It’s doing it with real time content that’s being created on the web. It’s not an old outdated model [00:29:00] and. And I trust those answers rather than a whole bunch of blue links, some of which may be paid to be put at the top or whatever. I think it’s going to disrupt search. I think it’s going to disrupt search advertising.

Um, we’ve got some really interesting monetization that we’re doing of Bing chat. Um, but, uh, I don’t know how this is going to evolve. I do agree with you that at the end of the day, there’s not going to be substitute for original content that gets created. And I think that’s going to have even more importance.

Not just in writing, but I’ll give you another example. So I know that AI is being used to create music. And it’s being used oftentimes in the same sort of way that we were just talking about it, where it just sort of gets you started and maybe it’ll add some things here or tweak some lyrics or whatever, I think as AI is used more of a music and, and, you know, even if AI is being used to create music [00:30:00] without any human real involvement, other than a prompt, it’s going to mean that.

Live music is going to get more important and more interesting. And, you know, you saw the kind of thing I maybe that you too just did in Las Vegas in the, in the Giant Dome. It’s going to put experiences that are real and human and interesting like live music. Like, you know, dance, like building your own surfboard or something like that, even more important, um, because there’s no substitute, like you’re never going to be able to substitute standing in front of an actual band playing actual music, even if AI might be a part of it.

And I think those kinds of things are going to become more important over time. So I agree with you. Original content of any type, I think is going to be more important as we go forward. I hope it is anyway.

Sushant Misra of TrepTalks: For sure. So you’ve been working, I mean, you’ve had your full-time job for a long time and you know, you have, um, played with entrepreneurship , [00:31:00] which one do you prefer?

Um, and, um, of course you’re still working and, but do you, do you see yourself becoming a full-time entrepreneur in the future, or do you like just really love working at Microsoft? That , that’s kind of your.

David Dennis Ventana Surfboards and Supplies: Yeah, yeah, both. I mean, I had a startup in tech 25 years ago that failed miserably. It was during the first dot com boom and it busted on us.

Uh, but I built built up enough experience there to wind up going to Microsoft, which is great. But I mean, the startup was a failure and I don’t think I would do that again. I love Microsoft. I love the new version of Microsoft under Satya Nadella. It’s just a phenomenal place to work. But I also love the entrepreneurial side.

Now within Microsoft, we have small teams and we get to do kind of entrepreneurial things with the large, the support of a large company. But I also love the, the, the entrepreneurship that I, you know, [00:32:00] have with Ventana. And one of the things I love is building a brand. I love marketing. I love sales. Uh, I love business development.

I love partnering. And I get to do a lot more of that in the, in the way I want to do it with my control in Ventana. And so I think I’ll probably do both. At some point, I might do more with Ventana if I actually retire from Microsoft and I’m 54. So that’ll happen at some point, but I don’t know yet. We’ll see.

Sushant Misra of TrepTalks: Um, in every entrepreneur’s journey, there’s always. Mistakes made, lessons learned, failures. Um, have you had any big kind of setbacks, uh, you know, since you’ve been running Vantana that you, that was a big learning experience for you? What did you learn from it? And what can other entrepreneurs learn from your

David Dennis Ventana Surfboards and Supplies: mistakes?

I think every time we fail at something. It’s because, and we do everything on small scale. We’re a small company. We, you know, we start with small runs of products and then we test them to see we have a new product about to come out, [00:33:00] um, this later this month. Uh, and we’ll, we’re doing a small run of it and we’ll see if it works.

But every time I try to like, if I assume like this thing is really going to work and then I order too many of them or, um, I print too many of them or a lot of them, and it doesn’t work. I’ve always sort of stuck with inventory or, you know, I’ve invested money in something that I was sure was going to be great and it wasn’t.

And so every time that happens, I go back and I say, what could we have done to learn and understand whether this could be successful by talking to customers, by putting out. You know, pre orders by asking feedback from our customer base on options that we might have for a certain product or a new product altogether and iterating our way into success as opposed to assuming we’re going to be successful.

The thing that I see entrepreneurs do way too much is believing their own. Their own marketing, you know, they, this is going to be the greatest thing and here’s why, and they get so passionate and excited [00:34:00] about it that they put all kinds of investment in it and it fails miserably because they didn’t actually do the hard work to do the research and iteration to make sure that it was going to be successful before they pour their life into it.

Every time I think about leaving Microsoft, I go, to Ventana surfboards. com slash TEDx, it’ll redirect to the YouTube link. And it’s called don’t quit your day job. And so I definitely will not quit my day job until it, unless something really big happens with Ventana and I know it can take off and support me, but I’m not going to make an assumption that that’ll happen unless we iterate and start small, uh, in ensuring that we’re going to be successful before we go and put a bunch of resources in that.

I think that’s

Sushant Misra of TrepTalks: a great advice. Um, unless somebody knows that, you know, they have found that product market, like they, they have discovered that market. That’s right. Um, I think it’s a great advice to to continue your [00:35:00] job because otherwise it’s like, uh, there’s the risk outweighs the rewards. I

David Dennis Ventana Surfboards and Supplies: think the other failure I have is that I.

I try to control too much myself. My partner and I have very distinct skills. Like I can’t cut wood straight. And so he’s great doing all the artisanship and I’ll building the products. Um, and I do, you know, way too much, like what I really need to do is bring on and we need to bring on a couple more people.

And maybe as partners in the company and just let them run. And I guess I I’ve, I’ve got to get over the fact that I, you know, sometimes don’t want to give up control. Um, if I were to ever, you know, start Doof Ventana full time, I’d have to do that. Right now it’s, it’s more of a fun project.

Sushant Misra of TrepTalks: So, I mean, um, to follow up on, on that point, what is your team right now?

Are you just the two people or do you, um, do you have someone who’s kind of helping you with, uh, uh, marketing or, uh, fulfillment and these kinds of [00:36:00] things? I do

David Dennis Ventana Surfboards and Supplies: everything other than, you know, not everything. The building of the products is really a lot of work, but, um, all the social media, all the blog posts, all the e commerce management, even fulfillment, I do all of it.

Sushant Misra of TrepTalks: Your fulfillment is in house. Okay. Well, yeah.

David Dennis Ventana Surfboards and Supplies: And again, we don’t do a ton of volume online. Um, most of what we do is event. So I’ll do, we’ll do a big order, you know, whatever, make a bunch of products and we’ll do a big event. We’ll do a couple over the holidays. Uh, and so most of our fulfillment isn’t really fulfillment cause we’re selling literally direct face to face.

Um, but yeah, I mean, I just, sometimes on a, you know, a break between meetings, I’ll be printing out labels on ship station or through Shopify and yeah, at some point, obviously if we scale, I won’t be able to do that. Well, very nice.

Sushant Misra of TrepTalks: Um, Now I’m going to move on to our rapid fire segment in this segment. I’m going to ask you a few quick questions and you have to answer them maybe in a couple of words or a sentence or so.

Um, one [00:37:00] book recommendation for entrepreneurs, uh, and

David Dennis Ventana Surfboards and Supplies: why? Uh, the lean startup, because it’s all about, uh, iteration and starting small and, um, learning from data. And entering your way into success. Very, very,

Sushant Misra of TrepTalks: very nice book. Yeah, for sure. Uh, an innovative product or idea in the current e commerce, retail, or tech landscape that you feel excited about?

David Dennis Ventana Surfboards and Supplies: We talked about AI. I’m just extremely excited about the potential for AI. Um, as far as e commerce, I just have never found a tool that’s as powerful and useful and user friendly as Shopify. Yeah, for sure.

Sushant Misra of TrepTalks: Uh, a business or productivity tool or software that you would recommend or a productivity tip besides the Microsoft, uh, uh, office suite.

David Dennis Ventana Surfboards and Supplies: Wow. There’s so [00:38:00] many. We, we, I did a presentation once about all the technology that we’re using behind the scenes with artisan surfboards. Uh, and there’s just so many of them. I got to go back to AI, like the thing that I’m finding right now, that’s accelerating my productivity more than anything, creating ad copy, writing blog posts, editing content, uh, creating images, even use it, creating images to give our artists that we work with around the world, inspiration.

It’s it’s all ai like that’s what i’m most excited about and that’s where I think the most productivity enhancers are right now Uh

Sushant Misra of TrepTalks: another startup or business in e commerce retail or tech that you think is currently doing great

David Dennis Ventana Surfboards and Supplies: things I I always look to patagonia. That’s that’s been I think they’ve got a good online model, but they also um for us They figured out how to scale sustainability, or at least they have a pretty good story around sustainability.

It’s not perfect. And they’ve always been, um, they’ve always been an inspiration for us.

Sushant Misra of TrepTalks: A peer entrepreneur or business person whom [00:39:00] you look up to or someone who inspires you?

David Dennis Ventana Surfboards and Supplies: My dad. So my dad was one of the, uh, my dad, Steve was one of the first entrepreneurs, one of the first software entrepreneurs in the Silicon Valley.

He started his first software company in 1972 before people even knew what software was, many of them. Uh, and so he’s. He’s been an inspiration. I grew up around in the tech industry. Dinner table conversation was always about entrepreneurship and, um, the technology industry. And so I, he’s always been a role model for me.

Sushant Misra of TrepTalks: And final question, best business advice that you have ever received, or you would give to other entrepreneurs.

David Dennis Ventana Surfboards and Supplies: If you don’t have to take investment, don’t. We, uh, and I’ve had that from several people, but early, early on in Ventana, we met with the founder of North Face, the apparel brand. And, uh, TapClop was the gentleman’s name.

And he said, if you can grow this on your own and keep control, um, don’t take on investment and [00:40:00] be beholden to others, obviously, if you really want to scale, you’ve got to do that. Um, but for us, at least at this stage, it’s been nice to not have to answer to other people.

Sushant Misra of TrepTalks: I think that’s great advice. And I’ve also heard that from a few other entrepreneurs before.

Uh, I mean, ownership is definitely, I mean, if your goal is to not just the control, but also, you know, the, um, To get the rewards of all your effort of entrepreneurship at the end. I think ownership definitely matters quite a bit. Um, well, David, those were all the questions that I had. Um, thank you so much for sharing your story and very interesting story and interesting product.

Um, if anybody wants to check out your products, what is the best way to do that?

David Dennis Ventana Surfboards and Supplies: Ventana Surfboards, V E N T A N A, VentanaSurfboards. com and Ventana Surfboards on every social media platform you can imagine and probably some you can’t. Awesome.

Sushant Misra of TrepTalks: Well done, David. Thank you so much again for sharing your story and I wish you and [00:41:00] your business a lot of good luck and thanks again for joining me today at Trip Talks.

Really appreciate it. Thanks, Sushant.


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