[Venture Capital Series] Private Stock Needs a Market Too With Sim Desai

Sim Desai is the Founder and CEO of Hiive, a marketplace that provides liquidity for private company shares. Since its commercial launch in 2022, Hiive has surpassed $5 billion in closed transaction volume and reached a $123 million revenue run rate while maintaining profitability. With nearly two decades of experience in private equity and secondary markets, Sim is passionate about bringing greater transparency and efficiency to the private-company secondary market.

Here’s a glimpse of what you’ll learn:

• [3:09] Sim Desai on Hiive’s role in turning private-company liquidity into an asset
• [9:07] Exploring the Hiive50 as a barometer for pre-IPO companies
• [15:51] Why the private secondary market has exploded over the past 15 years
• [18:05] Hiive’s journey to profitability and over 100% annual growth after launch
• [23:36] How companies like Kraken enable passive stock trading through Hiive
• [37:55] Hiive’s white-glove approach to venture funds and large institutional transactions
• [43:53] Sim’s approach to using competitor intelligence as a key entrepreneurial resource

In this episode…

What if employees and investors had a clearer path to unlock the value of private company shares before an IPO? As private markets continue to grow, what would it take to make liquidity more transparent, efficient, and accessible?

For Sim Desai, a private markets and secondary-market expert, technology can transform an opaque, fragmented private share market into a more centralized, automated marketplace. He highlights how structured liquidity options, the Hiive50 index, and a dual-sided marketplace can give shareholders greater access while allowing companies to maintain control. These innovations bring greater transparency, efficiency, and flexibility to private market transactions. Sim also shares lessons from building trust, creating network effects, and using automation to scale.

In this episode of the Inspired Insider Podcast, host Dr. Jeremy Weisz sits down with Sim Desai to discuss the evolution of private market liquidity. They explore private stock trading, the Hiive50, and employee equity access. Sim also shares lessons on competitive intelligence, growth, and entrepreneurship.

Resources mentioned in this episode:

• Sim Desai on LinkedIn
• Hiive
• Perplexity
• PolyMarket
• Databricks
• Lambda
• Ripple Labs
• Anthropic 
• Kraken
• Stripe
• Sapphire Ventures

Special mention(s):

• Matt Lawson on LinkedIn
• Sarah Huggins on LinkedIn

Related episodes:

• “Automation Solutions with Wade Foster Founder of Zapier” on Inspired Insider Podcast
• “Pipedrive: Brain Surgery, Married, & Moved Company from Estonia to U.S. All at Once – with Urmas Purde [Inspiration]” on Inspired Insider Podcast
• “[SaaS Series] Revolutionizing Online Forms and Productivity With Aytekin Tank of Jotform” on Inspired Insider Podcast

Quotable moments:

• “Our vision was to create a central place for private company stock, making life easier for shareholders and employees.”
• “We make liquidity an asset, not just a challenge for companies to manage.”
• “Centralizing capital flows and strengthening network effects creates greater opportunities for growth.”
• “Entrepreneurship is the highest professional pursuit — creating and building value in the world.”
• “A central platform gives employees the freedom to realize their stock’s value without waiting for an IPO.”

Action steps:

1. Monitor competitors and market trends to uncover new opportunities: Regularly tracking industry movements and competitor activity can provide valuable insights for strategic decisions and innovation.
2. Build relationships across all sides of your marketplace: Strong connections with companies, investors, and other stakeholders can strengthen network effects and drive sustainable growth.
3. Simplify complex processes through automation: Streamlined workflows and automated transactions can remove barriers, reduce uncertainty, and create a better user experience.
4. Adapt your strategy based on feedback and market needs: Evolving your approach and building collaborative relationships with key stakeholders can strengthen credibility and support long-term growth.
5. Participate in industry events to accelerate learning and connections: Conferences and specialized communities can provide valuable insights, relationships, and opportunities for growth.

Episode Transcript

Intro 00:15

You are listening to Inspired Insider with your host, Dr. Jeremy Weisz.

Dr. Jeremy Weisz 00:22

Dr. Jeremy Weisz here. I am the Founder of InspiredInsider.com, where I talk with inspirational entrepreneurs and leaders. Today is no different. I have Sim Desai of Hiive. You can check them out at Hiive.com. Before I formally introduce you, Sim. I always like to point out other episodes of the podcast people should check out. You know, this is an interesting episode actually kind of it’s a dual-sided marketplace. They have amazing companies listed. You can check them out. The Hiive50 Index. They also have investors coming in.

So I was thinking, you know, one of the interesting episodes, one of the co-founders of Zapier on the podcast, Wade Foster. That was an interesting episode. One of the co-founders of Pipedrive was also good. They, I think I had them on some of they were 10,000 customers. Now they think they’re over 100,000 customers. The founder of Jotform and he talked about how they got to 25 million plus users off of a freemium model, product led marketing with that and so many more on InspiredInsider.com, this episode is brought to you by Rise25 and The Podcast Consultants.

We help businesses connect to their dream relationships and partnerships. We do that in a few ways. We’re an easy button for a company to launch and run a podcast. So we do the strategy, accountability and the full execution and production, you know, so for me, the number one thing in my life is relationships. I’m always looking at ways to give to my best relationships. And I found no better way over the past over 15 years to profile the people and companies I most admire and share with the world what they’re working on. So if you have questions, you can go to Rise25.com or thepodcastconsultant.com, and you can email us [email protected] to learn more.

I am really excited and big thank you to Matt Lawson for making sure this happened. Sim Desai has more than two decades of experience in late stage venture secondaries. He has been building Hiive since 2021, and Hiive connects capital with opportunity in the market for late stage private company investments. And so since its commercial launch in 2022, Hiive has facilitated more than 5 billion. That’s with a B. That’s correct. In closed transaction volume across a broad range of private company securities. And really what that helped is unlock value in what has traditionally been illiquid asset class, right?, completed high funds include many, but Perplexity, space and many more., and Sim, thanks for joining me.

Sim Desai: 02:57

It’s a pleasure to be here, Jeremy. Thank you for having me.

Dr. Jeremy Weisz: 03:00

So let’s start off with Hiive and what you do. I’m going to pull up the website and so people can see it talk about Hiive and what you guys do.

Sim Desai: 03:09

Yeah. So, you know, that, that phrase that you see there is a headline, we make liquidity an asset, I think in many ways really captures, sort of our value prop to, to one of our most important stakeholders, which is the, which is the private company itself. And for those people who are really familiar with, this market, they understand that, the private company, unlike in the, in the public stock market, the company management of private companies is really at the center of, of trading and liquidity and investing in the company because, the management typically needs to approve transfers.

And so there’s a necessary step in which the company has to bless these transactions. And so our pitch to private companies is we make liquidity an asset. We help you turn liquidity into something very positive for your business. In terms of our business today, we have a range of different formats. We have formats where companies can be very passive in the process, where they just enable their shareholders to trade on our platform, buying and selling stock, and then beyond that, we also work with companies to develop, you know. Top down liquidity programs such as tender offers and other types of managed programs where the company sets.

You know, a certain set of rules around liquidity, whether that’s a point in time transaction where there’s a fixed price offer that’s made to shareholders, or they allow, investors and shareholders to trade the stock on an on going basis, subject to limitations, like, let’s say, a minimum price floor or certain approved buyers only, and so on and so forth. As a result of managing that market. We’re also able to offer investors a broad range of investors access to these opportunities. And that’s it. You know, to your point of the dual sided marketplace that is, you know, the other side of that, of that equation.

Dr. Jeremy Weisz: 05:10

You know what’s interesting? Just talk about the problems that you solve because you solve for the company, but also people that may own stock in the company, but they can’t trade it because it’s not publicly, you know, able to.

Sim Desai: 05:28

Yeah. So, you know, our vision when we launched this platform was the idea that you could create a central clearing place for private company stock. Some companies allow their stock to trade quite freely. And in those cases, you know, it’s valuable for, for a shareholder and employee to be able to come to a place and say, hey, what’s the market price for my stock? How do I find buyers for my stock. You know, what’s the process for completing the trade? All of that is such a black box for most private company shareholders.

Our platform enables them to really seamlessly go through that process, from price discovery to finding a buyer to completing the trade in a, in a quite an automated way. In fact, a seller can go through that entire process without ever speaking to a human being or even exchanging an email using our platform. So I think we’ve automated that process to a greater extent than anybody else. In terms of private companies who run top down programs we’ve also automated the process of executing on a tender offer.

And in that case, you know, a shareholder isn’t necessarily participating in like a free market transaction. But what happens is we set up the platform so that, all there’s a, there’s a fixed price that’s communicated to all of the eligible sellers for that program. And, and then, and then the sellers can then elect whether or not to participate and sell their their shares at the specified price. So yeah, the idea was to deliver something that could unlock, you know, make life a lot easier, more streamlined, more centralized for people participating in these transactions.

Dr. Jeremy Weisz: 07:11

For the top down liquidity program, like what kind of company? Who’s a good fit for that?

Sim Desai: 07:18

You know, companies who generally are looking to exercise exert like a very high degree of control over liquidity, you know, they might want to, establish a fixed price. They may not want to allow shareholders to trade on an ongoing basis, for that type of top down program. You know, a tender offer is a great format. They can also have trading programs through top down programs. So what that means is, for example, you can have a trading program that has certain limitations, i.e. you can only trade, one month every quarter. You can only trade above a certain price. You can only trade as a seller. You can only trade with certain buyers. As a seller, you can only trade a certain percentage of your stock in a given year. You know, you can have a traded market that is subject to a range of rules. And that’s sort of, let’s say somewhere in between a totally free market and a totally controlled market.

Dr. Jeremy Weisz: 08:18

So I’m one of my favorite parts of your website is the Hiive50. Okay, so I want to talk about the Hiive50 and how you came up with this idea and how it works. But I will say, I like just to go and you people can check this out. If you go to Hiive.com/Hiive 50, you can check out if you’re listening to the audio, there is a video portion and we’re looking at it. But just for me just to discover companies and maybe I live under a rock for something that I’ve never heard of that I should know about. Okay. So I was like looking at this this morning, I’m like, okay, or I’ve heard, but I haven’t really dug deep on this. Right. And so, you know, like, for instance, I keep hearing about whatnot. I have several people who do stuff on whatnot. And I’m like, oh, this is number 39 on here. I should probably look into it a little bit deeper on how people are using it, what it is. So talk about the the Hiive50.

Sim Desai: 09:07

Yeah. So the Hiive50 is, it, it’s a, it was a, it’s a somewhat ambitious project that we launched a couple of years ago to effectively create a barometer for the pre IPO market. And when I say pre IPO, obviously what I’m referring to is companies that are highly valued that are private, that are venture backed, not all of them will be going public anytime soon, or let’s say most of them won’t., but these are, these are the, the giants of the private market, right? Companies that are valued typically well above.

Dr. Jeremy Weisz: 09:41

I mean, sign me up for Stripe when that thing goes public. Exactly.

Sim Desai: 09:45

Exactly. And so in terms of inclusion. So to qualify for this list, you have to be like highly valued. You have to be you have to have secondary activity, but to qualify, sorry to get into the list. It is based on the top 50 companies by trading volume in the prior six month rolling period. So every quarter we up, up, up update this list, we refresh it and it is determined by the trading volume or quote unquote liquidity of that stock in the last six months as of the date of the reconstitution. And then we take each stock and we equally weigh it. So we don’t, so unlike, public market, public index, where you’ll often see market cap weighting, i.e. the, the, the, the index is weighted by the size of the issuers.

We don’t do that in our case. And look, there’s an argument for doing it. And I think that’s a, let’s say, a higher complexity project to pursue that. But for now, what we do is we take these top 50 companies and we equally weigh them. The idea is that the the sum total of that the is is enables you to get an idea of how the market is trending. So, you know, you see companies on this list, some of them are trending down in terms of price and others are trending up. But overall, you get an idea of the direction by taking that, that aggregator, that that aggregate into the Hiive50, you get a sense of the, the total direction of the market. So, and so that’s what that chart is at the very top.

Dr. Jeremy Weisz: 11:19

Which one of these, I don’t know, surprises you at all? Like we’re looking at number one here, PolyMarket here, Databricks Lambda. We have Ripple Labs, Anthropic, Kraken, Perplexity AI or any of these that surprise you when when obviously you’re just talking about numbers here. And, but when looking at it like, I’m kind of shocked that this is on the, the Hiive50

Sim Desai: 11:45

I mean, like, I wouldn’t necessarily say any of these names surprise me. These, these names are, These are the one thing to to understand is that this is based on our own data, right? So it is this this set of 50 companies is limited by which are the companies that are trading through Hiive. So for us, it’s obviously not surprising since we, these are companies that are trading through Hiive and therefore. You know, they’re going to show up on the list, whether or not this particular ranking is like a good ranking or reflective of the overall market, that’s a very different story because our ranking is only determined by our transactions, which is obviously a sample of the total transactions that are happening in the market. And therefore this ranking of 50 should not be viewed as sort of anything, like the Bible in terms of, you know, the actual truth of the order of in which these companies should be ranked. And, you know, there’s, again, it is determined by liquidity and how much trading happens. So if a company is highly restrictive of trading, then you may not see it highly ranked here on this list.

Dr. Jeremy Weisz: 12:52

Yeah. The two that surprised me were The Farmer’s Dog. Okay, so and, Whoop for some reason, right? Because you have them on the list with things like Stripe and, you know, some of these other tech companies, right? Yeah. So it was pretty interesting. What are we looking at here? So like we have ranked, but the company price trend current live orders..

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