Foreseeing The Future Of Commerce With Stephanie Nwokolo Of OpenSky Ventures

With the advent of AI and the seemingly endless innovation of technology, the future of commerce could be tremendously exciting. This is why OpenSky Ventures strategically invests in commerce enablement technology and disruptive consumer brands. Joining Scott Kelly is Stephanie Nwokolo, a Principal at OpenSky, to talk all about their fund and the powerful synergy between portfolio companies. She explains how their firm’s founders leverage decades-long experiences and a deep professional network to find promising early-stage founders who are making huge waves in the modern world of commerce.

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Foreseeing The Future Of Commerce With Stephanie Nwokolo Of OpenSky Ventures

In this episode, we got a chance to interview Stephanie Nwokolo of OpenSky Ventures and she’s going to share a little bit of her background of her unique career path. She was at PIMCO and Lionsgate and co-founded her own non-alcoholic beverage company before joining OpenSky. OpenSky is led by founders and operators, Josh Resnick and Josh Payne, who have a great track record of growing, scaling and exiting consumer and consumer brand companies, primarily investing at the pre-seed and seed stages.

As you’ll learn in the interview, the firm’s value add comes from their decades of operating experience, their strong network of connections to stakeholders and a natural synergy between their tech and brand portfolio companies such as introducing generative engine optimization for Gumshoe AI and other portfolio brands.

Stephanie highlights that the company’s portfolio has been very vast by combining their portfolio companies that provide commerce technologies to consumer brands and the consumer brands that are utilizing these eCommerce technologies. Currently, the fund is raising their Fund 2, looking to partner with family offices and high-net-worth individuals.

They are aiming to leverage their successful Fund 1 performance, their deep domain expertise and the ability to navigate market disruptions like AI and GLP-1s. As you’re going to learn from this interview, there’s a really great integration between the technology that powers brands and the brands that use this technology and how they’re investing in both to provide benefit to both. I’ll also have some key insights and takeaways from our interview.

I’m excited to introduce Stephanie Nwokolo Hussey from OpenSky Ventures. Welcome, Stephanie.

Thanks, Scott. Great to meet you.

Looking Back To Stephanie Nwokolo’s Career Journey

Nice to meet you. Tell us a little about your background prior to OpenSky.

Yeah, so I started my career at this place called PIMCO, an investment management firm. I initially started working on this on the product strategy team for this fund called Manage Volatility, which was a systematic strategy that traded equity features on implied volatility. It was an $8 billion fund. I learned a whole lot because the people at PIMCO are just really intelligent but totally different asset class.

I also worked on this team called the solutions team, which just worked with institutional clients, pension funds, endowments, etc., helping them with any asset allocation questions they had and helping them understand the drivers of risk in their portfolio. I learned a lot about all the different types of asset classes and the types of questions and concerns that institutional clients had. That was really great from a learning perspective, but it wasn’t really something that I enjoyed and I learned that really early on, but stuck it out for a few years.

After that, I always said I wanted to work for a “real” company, so more of an operating company. I had an interest in the entertainment industry so that led me to go to Lionsgate where I worked in finance and strategy on the motion picture group. While I was there, my best friend and I at the time started a non-alcoholic functional beverage company. It was called Camby Clean Cocktails.

We had three flavors. They were more mocktails with adaptogens infused. It gave you what we called abuse booze-free buzz. We got into a couple of retailers in LA, did the farmer’s markets, built out a proof of concept and that’s what really sparked my love for early stage and the founder’s journey. I met so many amazing founders while I was pursuing that and I learned so much about myself because I had always thought of myself as more of a finance and operations person.

I realized through that that I could wear multiple hats, whether it’s like talking to people and building relationships to create sales or thinking about marketing and branding. For me, that was really pivotal for me. After doing a little bit of soul searching and it didn’t work out with my co-founder, I would really advise founders to be very critical of who you choose a co-founder. That was my number one lesson that I took away from that.

Through that, I realized after Camby didn’t really work out through some of those issues, I really wanted to stay in the ecosystem and I had gone through this other process where I was like, “Maybe I can become a founder again and try it.” It just felt forced and my heart wasn’t so into it right after that experience. It made me realize that maybe I should be on the other side of the table and I could empower founders without necessarily having to be a founder. I got connected with my GPs, Josh Payne and Josh Resnick who are the GPs of OpenSky Ventures and that’s when I started my time at OpenSky in September 2024.

How OpenSky Ventures Was Founded

It’s a great background. It’s interesting, there are several parallels to us in that regard. I was a fixed-income trader for a while in my early part of my career and it’s not the most exciting part of the business. I definitely understand that. I was in the entertainment business, I owned a record label, I had one gold record to my name, so I understand that piece. We’ve actually had several food and beverage investors on the show, so I love the backstory, so appreciate that. Let’s talk about OpenSky. Talk about what the fun thesis is, what kind of founders you’re investing in one industry and things of that nature.

Of course. To give a little bit more context, Josh Resnick and Josh Payne are also founders and operators and Josh Resnick started his entrepreneurial career with Pandemic Studios, which exited to EA for $860 million. Really great success there as a founder. After that, he started a family office where he started investing in different types of companies, really consumer-focused, but I think he has over 50 angel investments from that.

While he was doing that, he started Sugarfina, the luxury candy company. Obviously, for those who know, it’s just an iconic brand. Something that when you know it, you see it and it just has a special place in your brain. Josh Payne founded StackCommerce, so he exited that to TPG in 2020. That was more on the commerce enablement side in the early 2010s, connected brands to publishers.

From that, they are just true founders and operators who just know how to scale businesses and they decided to join forces. They had Angel invested together. Funny enough, Josh Resnick had invested in Josh Payne with StackCommerce. They’ve known each other for a really long time and wanted to help their portfolio companies in the context of a fund to scale and share their best practices.

OpenSky Ventures started in 2023 and the focus is the future of commerce. Sixty percent of our portfolio is centered around commerce enablement technology, so any technology that consumer brands use to either operate more efficiently, market better, etc., and 40% is focused around consumer brands, so the brands that actually use the technology. There are a lot of natural synergies there. We’re early stage, so pre-seed, seed and a little bit of Series A, but really the focus is pre-seed and seed.

The Future Of Commerce With The Advent Of AI

You talk about the future of commerce, so tell me what the future of commerce looks like in the advent of AI, in your opinion.

I think AI plays a really big part of it. It’s opened up these areas of innovation for these operators to come in and help these brands operate more efficiently. Even the brands themselves, you are seeing more solo founders find success, you’re seeing them achieve profitability a lot faster. I think you’re seeing a lot of different seismic changes with the way both the brands and the tech side interact with each other and bring a little bit more efficiency to a market that has was pretty efficient to begin with.

I would say commerce has always found equilibrium, but I think with AI, it’s just added this whole layer of efficiency and speed to the way people can do things. I think you are seeing a lot of adding the human layer to a lot of aspects because commerce is so people-focused and you want to feel like you’re talking to a person if you need to return something or you’re dealing with customer service or anything like that. I think a lot of these agentic AI tools are focused on that aspect because that’s what really drives retention and also just loyalty to the brand or whatever service you’re dealing with.

What OpenSky Ventures Is Looking For In A Founder

Yourself and the GPs obviously have a founder background, so in addition to industries and stage, maybe give me a profile of the ideal founder that you would invest in. What are the attributes of these founders?

I think a lot of times, with pre-seed, seed, there isn’t a lot of data to go off of. We just describe it as someone who runs through walls to get what they want done and I think that’s just the type of hungry, really ambitious person that believes in what they’re doing. Also, I think there’s an aspect of founder market fit, like why is this problem specific to you? Why are you the best person to solve this problem? What about your experience makes it so that you have the expertise better than maybe some of the other people in the market who have similar backgrounds to solve the problem and really bring it to scale?

I think those are some of the qualities we look for from a more qualitative perspective. Quantitatively. I would say a lot of our founders skew age-wise all over. I don’t think we skew younger, I don’t think we skew older. We’re agnostic to that part. I do think it’s really important, especially on the tech side, where on the pre-seed side of things, we really like a seasoned entrepreneur, but that’s not always the case. Sometimes you find someone who really gets it and is really able to bring the pieces together.

Success Stories At OpenSky Ventures

Obviously, yourself and your partners have had some great success but let’s talk about OpenSky. Any success stories or any portfolio companies that you’re excited about?

I think we have quite a few. It’s actually hard to choose just a few. I can probably list 7 or 8. We could be here all day with me talking about it.

We love all the children but talk about some of the ones that have done something really cool.

On the consumer side, we invested in Fishwife. It’s this tinned fish company and the founder is just amazing. We invested in 2023 and since then, she’s just been able to grow the business remarkably. She’s in 1,000 Kroger’s and lots of Targets and growing her footprint in Costco. Just really growing the business in a way that feels sustainable and manageable but also impressive from a VC perspective. That’s one that I feel quite proud about, especially because it just encapsulates what we mean by disruption in consumer.

It doesn’t necessarily mean that you’re completely creating a new category. What she did was she went into a sleepy category and just reinvigorated it. If you look at the branding, it’s really beautiful and ornate and it just captures your eye when you’re walking in a store or when you’re online and you see it. I think they’ve done a great job with all parts of what you want to see from a consumer business.

Levanta is an example of another portfolio company more on the tech side that’s just done really well. They basically are an Amazon storefront that helps connect brands to more affiliates. Levanta basically does affiliate marketing for Amazon but they’ve expanded beyond Amazon since then and they’ve done a great job with just tapping into the affiliate marketplace there. It’s just, again, another example. Those founders were repeat entrepreneurs as well and they’ve done a great job of scaling it in a way that feels very manageable but also at the same time reasonable.

I think those are good examples. Siena AI is another example on the tech side, they are more agentic CX agents and so basically when a customer comes to a brand and they’re like, “I need to make a return,” or, “I’m not happy with this size,” or something’s wrong after they purchased and engaged with the brand, Siena comes in and they have a chatbot that communicates to you like you’re human.

That highlights one of the themes that I was talking about earlier. They’ve done a really great job with brand integration and just being able to really make sure that they’re addressing the problems the brands have and making humans and the humans/customers feel like they’re being heard. Obviously, that helps the brand by increasing retention, LTV, etc. Those are just a few of the company highlights that we have.

Building A Natural Synergy Between Portfolio Companies

I want to delve a little bit into the value add because the whole genesis of creating this show was to cast a light on the non-monolithic traditional invest venture capital firms. What I’ve found over the course of this show is that there’s some value add that comes to the table. Obviously, you’ve got founders that are in consumer companies and now, obviously, your fund is investing with previous founders in the consumer space. What other things can you as OpenSky bring to the table in addition to capital for these founders you invest in?

I think first off is with decades of experience between Josh, Josh and also myself. We have lots of connections to not just investors but different people and stakeholders who can really elevate your business or help you where you really need help. We are able to leverage that to help these brands and tech companies really just make it easier for them to get to that next level.

I think what’s really notable about that is the network connections, whether it’s an agency or anyone else that really needs the help. I think that there’s also that natural synergy between our portfolio companies, so the tech side and the brand side. The tech side gets introduced to our brands on day one and our brand side gets to understand more about what they can do and enhance within their tech stack to better perform and better address what the problems that they’re experiencing as they scale.

I think Josh Resnick really is one of the best brand people I’ve met in my life. He just understands what it’s like to really build a brand and make it a generational brand. I’ve seen him go in and completely revamp brands, refresh them. That innate sense of human attraction to a brand, he just creates that. Josh Payne on the marketing side and go to market side is just really incredible as well.

With that, I think they really address a lot of the key issues early-stage founders experience as they’re getting to that next level in their business and they help them get to that next level a lot smoother. I think the connections, again, are understated in terms of how many connections that we have and are able to bring to the founders when they really need those doors open the most.

I’m glad you brought that up. I was going to ask that as a question of the consumer port codes working with the tech port codes and I’m glad you brought that up. Do you have any examples of one of the consumer port codes that actually is working with the tech port codes and how that’s working out?

One of our portfolio companies is called Gumshoe AI. They’re a generative engine optimization. They help brands understand how they show up in LLM search. Whether it’s Perplexity or ChatGPT or Google Gemini, they help brands understand if I’m a 40-year-old mom, if I’m a 15-year-old boy, if I’m a 30-year-old woman, how do I show up when I look for Nike, for example. How do these people show up when they look for Nike and how do they stack up against other competitors in that space?

We introduced Gumshoe to our brand portfolio companies and most of them were just like, “Please sign me up. How can we show up better in LLM search and really take advantage of the space?” I think it’s really understood that that’s the way, that’s the future. That’s where search is heading towards and it’s really important for them to stay on top of that so that they can understand how they show up. I think there was a natural synergy there and I have a couple of other examples but I think that one was just one of the biggest ones where we really hit the nail on the head with addressing those brands and what they were looking for.

Investing In High Net-Worth Individuals

Let’s talk from the investor standpoint. A lot of our readers are LPs, family offices, and high-net-worth people that are looking to invest in venture. Can you share a little bit about the makeup of who the investors are in the fund now? Not by name but by category.

Fund 1 primarily are solely high-net-worth individuals. It’s hard to raise a Fund 1 and then get institutional buy-in, but I do think we built relationships there when we were raising for Fund 1 but Fund 1 like a startup is friends and family and friends of those friends and family. That’s how that Fund 1 is composed or comprised of.

For Fund 2, we’re actually going to start raising for Fund 2 soon, and so with that, we’re aiming for more family office involvement. We are hoping to get some early stage emerging manager programs from endowments as well. I think the focus will be high net worth individuals and the family offices as well. Obviously, like I said, endowments are welcome.

Why Choose OpenSky Ventures Right Now

For people looking at OpenSky and Fund 2, I always like to ask this leading question. Why OpenSky, why now?

I think our performance in Fund 1 just basically confirmed what you would expect from operators, angel investors who’ve had successful exits and who know how to scale businesses. We have the network to access these companies and then we’re also able to select the better ones and select the ones that we feel like are able to scale appropriately. We have that intuition and we’re able to use our network to figure out how is this come do the reference checks and customer calls and really understand and get to the bottom of it.

On top of that I think we’re able to add that value so to actually help them get to that next level. I think when you combine those three parts, our performance in Fund 1 has really shown that we know what we’re doing and then there’s a lot of synergy with what we’re doing. I think the domain expertise is really helpful and will continue to be a help as we go into Fund 2 in terms of just with the aim of writing bigger checks and having a bigger impact on our portfolio companies.

We’ll definitely be able to do that with the knowledge we’ve amassed over the last few decades collectively as a firm. I think this time right now, we’ve talked about AI, we didn’t talk about GL-1s, which are changing consumer a bit. I think those are two areas where it’s created a lot of disruption and innovation and areas that are ripe to look on to the next few years and invest in those areas. I think with that, it’s this interesting area we’re in with is AI a bubble? We don’t know. A lot of people are asking that question.

I think from the perspective of where commerce is, I think you’re seeing a lot of true value being built from these companies and they will stand the test of time. This is a really interesting time to be involved. With the consumer bubble that popped a few years ago, a lot of investors did leave the industry and from investing standpoint and so that left a lot of white space and we’re still taking advantage of that. We’re still getting these founders.

It’s hard for harder for them to find capital and raise than it was a few years back. Now I think it might be increasing a little bit in terms of the amount of capital open to them, but they’re still a little bit of white space there. I think we’ve done a great job of really curating it and being a place where founders feel like they can talk to other founders who’ve been there and understand the struggles. I think that those are the reasons why OpenSky now and just why OpenSky in general.

Try To Be Respectful As You Can

Any final thoughts or advice you want to share to our audience?

I think with founders, this is not necessarily the easiest time to fundraise, but I would say it’s never really easy to ask people for money. It takes a process but I’d say at OpenSky, we try to be as respectful as we can. Sometimes during IC, we’ll say, “When we were founders, we didn’t like that,” or the Joshes will bring that up and we just try to really implement that into the way we like to work with founders. I think we truly understand the fiduciary responsibility part of it as well from the LP side. I think that’s something that we don’t take lightly.

Every dollar we get from an LP, we really try to take it seriously. Not that we wouldn’t otherwise, but I think we understand that there’s an opportunity cost to every dollar that gets invested in venture, especially given the lack of DPI and the headlines associated with venture with regard to that. I think that’s something that we try to be very strategic with the way we approach it and we have a lot of different strategies with how we approach allocating the capital we are our LPs invest in us. Those are the two things. We’re excited for Fund 2. I think Fund 1 has been doing really well and we’re just excited to see how the future of commerce continues to develop.

Get In Touch With Stephanie And OpenSky Ventures

Where can people learn more about OpenSky and again, contact with you and the team?

OpenSky, we’re on LinkedIn, so if you search OpenSky Ventures, we should be there. In terms of contacting us, Hello@OpenSky.vc is great. We always check that email. We get the emails come directly to us. That’s a great resource. Also, if you want to follow me, you can add me on LinkedIn. I’m actually starting a podcast myself, so Almost Oversubscribed is going to come out in early to mid-2026. Watch out for that.

We look forward to that. Stephanie, thank you so much for being the show. For those reading, I encourage you to reach out to Stephanie, look out for her podcast and make sure you find her by her full hyphenated name. Stephanie, thank you being the show. I appreciate it.

Thanks, Scott. It was great chatting.

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We learned a lot of interesting things from my interview with Stephanie at OpenSky and there are some great key points that she focused on during the interview. The first one was for investors that look for operator expertise. OpenSky Ventures’ performance is attributed to their general partners background as successful founders and operators who leverage their ability to scale businesses and their intuition to select and support promising companies.

The other important focus that we discussed was having domain focus. It’s the firm’s focus on the future of commerce, which provides specialized knowledge, opportunities and ability to perform far better than their peers and then also mitigates the risk of their investment. They also really stress, and this is something that’s been a theme that a lot of the emerging managers, to seek value add beyond capital. What OpenSky has the ability to do to create synergy between its tech portfolio that they invest in and the brand portfolios that they invest in.

Many of the brands in their portfolio are using the technology of the not technology investments in their platform. It gives a really good opportunity not just to get the needed capital, but get the tools necessary to scale. The other thing is that we want to be key in looking at how they are tailoring market disruptions.

The firm is strategically focused and there is right for innovation such as technology using AI and the shifts in consumer behavior driven by things like GLP-1s, positioning for potential and significant growth. I encourage you to read this interview and take a look at what OpenSky is up to if you’re interested in investing in the fund. Stephanie shares her background. I encourage you to come back here next time. Before you do, make sure you like, comment, follow, and share.

Important Links

• OpenSky Ventures
• Stephanie Nwokolo Hussey on LinkedIn
• OpenSky Ventures on LinkedIn
• Hello@OpenSky.vc
• Almost Oversubscribed on Instagram
• Stephanie Nwokolo on X