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How To Secure Investors as an Entrepreneur

Raazi Imam is a Co-founder and Partner at Unlock Venture Partners, a venture capital firm focused on early-stage technology investments in Seattle, San Francisco, and Los Angeles. Raazi is also a Co-founder and the Chairman of the Board of Directors at Caiman Consulting, a management consulting firm that focuses on management consulting and digital marketing solutions.

Raazi started his career in mutual fund trading before transitioning to management consulting with companies like Arthur Anderson, Bearing Point, and Hitachi Consulting. Raazi has advised executives around the globe in a variety of industries including fintech and e-commerce, and is also an active early-stage tech investor.

Intro  0:04 

Welcome to The Future is Borderless podcast with David Nilssen, we feature top entrepreneurs and thought leaders from around the world, those who bring a global mindset and a unique perspective to their life and business. Now, let’s get started with the show.

David Nilssen  0:22 

Hey, David Nilssen here, I’m the host of this show. Here I connect with business leaders from around the world who have what I like to refer to as a borderless mindset. And this is a place where we can share ideas and innovations, best practices, things that can be used both in your personal and professional life, ultimately helping us grow in a rapidly changing world. Now this episode is brought to you by Doxa Talent. Doxa helps businesses to find full time highly skilled workers from all over the world. And as a result, these companies can scale faster increase margin and improve culture. The most common roles that they fill are things from virtual assistants, finance professionals, sales and service, even software engineers. And to learn more about Doxa you can go to All right for our show. I’m excited for today. Raazi Imam is the General Partner with Unlock Ventures a seed-stage fund focused on helping new entrepreneurs sort of launch and scale their businesses. Before Unlock Raazi was the CEO and chairman of the board for Caiman Consulting, which was a management consulting firm he founded in 2004 and was eventually acquired in 2019. Today, he is a senior mentor at Stanford StartEx incubator, and Raazi has a degree in management and information systems and finance from the University of Texas Longhorns. And he started his career in mutual fund trading, before moving to management consulting with Arthur Andersen and Hitachi. And along the way, he’s advised some smaller companies like Google and Facebook, Microsoft, eBay, even Capital One. So Raazi, it’s great to have you on the show.

Raazi Imam  1:55 

Thanks for having me. David, I’m excited to speak to you.

David Nilssen  1:59 

Yeah, it’d be fun to sort of jump into your journey here. Now, as I introduced you, I was talking that you’ve obviously started your career consulting was obviously very big companies. But I’d be curious to know, what was the moment when you started consulting, that you realized that you wanted to be an entrepreneur and sort of decided to take that leap into business for yourself?

Raazi Imam  2:16 

Yeah, I was living in Seattle, it was 2003. And one of my good friends at the time, Greg Long, and I were on this project, where we were literally Microsoft sending us all over Asia, to help them roll out a product. We were like, I think we could do this without the big company name and the brand, because there’s a subset of work that even these big companies need to get done on a local level. So what if we started a company that was focused on helping local consultants work with big enterprise companies and helping them solve their business problems, and that was kind of the genesis for Caiman Consulting. The other thing that we really thought we could do is the culture at these big companies, it’s like a machine, right? You’re just a small cog in a massive wheel. And we thought, hey, could we make consulting, take it back and make a little bit more human, a little bit more personable. And so Greg was in LA, I was in San Francisco, we both moved up to Seattle, started this firm Caiman Consulting. And that’s how we kind of got off the ground as we went and beg, Microsoft, allow us to consult with them. And here we are.

David Nilssen  3:24 

That was the sales strategy, go beg Microsoft, were they you’re anchored client was that thing, sort of how you sort of cut your teeth initially?

Raazi Imam  3:31 

They were, we had consulted with them through the big firms that we had been at the we understood the ecosystem of the market. The part we were sensitive about was we didn’t want to steal the companies that we had worked for as business. So the hard part for us was neither Greg or I were partners at the time, we were middle management at the, at these big firms. It was how do we walk into Microsoft and convince them to go hire two guys that have a good consulting background, but have nobody else on their team? And so, it took Greg about three, four months to pull it off. And I got lucky. And I did it in like two or three weeks. But that was the challenge.

David Nilssen  4:15 

I love that. So you guys were sort of swimming around the well, you were actually working directly for this larger consulting firm, you decided to move out but one of the sort of call it values or principles you guys had was do no harm, right?

Raazi Imam  4:28 

Yeah, we wanted to make sure we were doing business ethically, we weren’t stealing some other consulting firms business, we just didn’t think that was the right way to start a new business. So which meant we had to quit our jobs with nothing in our hands, go kind of tin cup and find the first client. And it was kind of scary, but it was kind of exciting. We were also young, dumb and blessed. So that made it easier.

David Nilssen  4:52 

Sometimes that ignorance is helpful. By the way, I love that we you know, obviously we’re in the business of helping companies to find talent international. And one of the big risks that you find there is that if people do well, then they’ll want to eliminate jobs in the US in favor of the cost arbitrage that they could potentially gain. And we’ve actually made that clear that that’s not the type of business that we want to work with, because we don’t want to do harm along the way. So I love that, because that was your philosophy. It Caiman, you guys ran that for approximately 15 years and then sold it. I’d love to hear about most of the time people tell the stories, the good stuff, right there was telling you like, oh, it’s so fun, we’ve got this great business, we had a successful exit, but I’d love to hear if there were any moments along the way that you felt like you had your back up against the wall are really pressed to make some tough decisions. And what was that like?

Raazi Imam  5:39 

Yeah, there was a moment, there was many moments, but there’s one that, sort of I can, it comes to mind, we were in the process of, we had hired an investment bank to help us facilitate the process. And there were a number of companies that wanted to acquire us, some wanted to buy us, some wanted to sort of co-merge with us. And there was this moment where our leadership team, a portion of our leadership team was like, we shouldn’t do this, like, we have a great culture, we’re going to be fine. And it was basically less sort of, like, my vision was, for us to grow and scale the business, we needed to have a bigger company to work with that could help us go global, as opposed to me trying to go global, and go work in Germany, or Singapore, or wherever. And so it was this moment where it was like, oh, my God, like, if this doesn’t work out, I’m going to rip the team apart. And so there was a lot of like, quiet and some tears, and some, like, just getting people aligned again, and saying, look, this is the future, we think, then thankfully, we closed our deal in November of 2019. COVID happened in March of 2021. So, thankfully for me, like, they looked at it when in March, and they were like, wow, this was a good thing we did, right?

David Nilssen  7:01 

Yeah, very good timing. Ii is funny, though. Like, I can imagine so many people thinking, like, my understanding, at least my belief is that people stay at companies, because they feel like they’re growing and developing as people and professionals, but they also feel really connected to the culture. And so when they can see around the corner, a things are about to change, and you never really know what’s going to happen, that can be really scary for a lot of people. So yeah, very interesting. How, what was it like for you, though? I mean, here, you’ve had this baby for 15 years. And you sign the paperwork, transaction close. Certainly it’s a life-changing event in one way, shape, or form. But emotionally, how did you deal with that? Like, I know, a lot of people that have sold their business and their identity is tied so closely to it that they sort of feel a little bit lost. But what was your experience in that?

Raazi Imam  7:45 

Yeah, I definitely felt that, like what you’re saying, sounds like maybe it’s come from a place that you understand really well. But, I felt there was this moment, a few months after the transaction closed, David, where I realized, like, you know what, this isn’t my baby anymore. And I’m really a custodian of the acquiring firm. In this case, it was called theater partners. I’m a custodian of their business in this new market that they want me to own and manage and run. So it was a bit of a relief, I think, once it sunk in, because it changed the way I thought about things. I didn’t approach everything with the defensive manner from then on, it was more like, oh, you know what, listen, this is their business. Let’s see if that works. Let’s see if that recommendation they have or that approach they want to take works. Then it was an important shift because Sia, historically, has acquired a lot of businesses. And that’s part of their growth strategy. And so I’ve also seen since then, this is two-plus years now, other founders not make that shift, and it’d be very painful for them once they’ve been acquired, because they still want to hold on. It’s not your company anymore.

David Nilssen  8:54 

Yeah, that’s going to be really hard transition for a lot of people, I try to think about what that’d be like, for me, if I were to be acquired from a larger firm then have to go effectively be an executive inside of that, when you’re used to calling the shots. And it’s about you’re a little bit more, sort of in the driver’s seat. That’s a big shift. Well, tell me a little bit about today. So you’re obviously a GP at Unlock Ventures. And in full disclosure, for those of our listeners, I am one of the limited partners in that fund. But tell me a little bit about why it made sense. Is that sort of being the next phase for you and your careers just to start a fund.

Raazi Imam  9:30 

Yeah. So the other two partners, Andy and Sanjay and I have been angel investors and had been angel investors for a long time. And so what that means is, we see interesting deals in the market, and we put in 10, 15, 20, 50, $100,000 into these startups. And we hope and pray that they go well. And then like 2015 2016, we realized, hey, you know what, that is not a winning strategy because you have zero so you can provide zero support to these startups, because it’s not your job, you’re not really putting enough capital behind it, you don’t have enough of an equity position, you’re not taking a board seat. And so we decided to go raise a fund or first fund and do it properly. And in the process, there were a bunch of things we had learned both being entrepreneurs, as well as angel investors that we thought would be valuable. And so that combination is sort of a got us interested in raising a fund and starting a fund and then going in investing. We’re like, 37, 38 companies into our portfolio now. Between fund one and fund two, so it’s been quite a journey.

David Nilssen  9:30 

Yeah, and what the investment thesis? Like, when you guys are thinking about which investments to make? What’s the sort of filter that you put on that?

Raazi Imam  10:44 

Yeah, so first and foremost, we’re very founder focused. So we have to really believe in the CEO, and usually the CEO, and maybe the small core team, we’re investing at the precede seed stage. So there’s, one, two, three people on the table, we really have to believe in that CEO. And so if the CEO comes to us referred, or perhaps they were, somebody we knew in our network, that obviously helps. But we go through a pretty significant diligence process and understanding that CEO, and that’s really, really important to us. And it’s really important to precede seed companies, because you’re really betting on that individual, and perhaps one or two other people on their team to determine the success because inevitably, whatever you’re investing in, is going to change, right? The model, the product-market fit, the product, the market. And so if you have a great CEO that has experience, and can build and lead a team, and get you through some of those difficult inflection points, it makes a big difference.

David Nilssen  11:39 

Yeah, I remember early on in my career, one of my mentors told me that once you read a business plan, it’s wrong. And so I can appreciate why it would be important to believe, the CEO is going to be able to figure it out. If you get the right sort of general direction, because we know that no matter what’s put on that initial investment presentation, it’s going to change over time.

Raazi Imam  12:03 

Yep. The second thing I would mention is, we like investing in it. So it’s all tech investments. And we like investing in companies that are thinking about data, and AI and how they build their products. So that’s also pretty important to us, because we feel like data is the valuable asset in the future. And if we’re investing in companies that are thinking about that, and they have proprietary data sets, or they’re using data for monetization, or data for helping segment customers, etc, we think that’s something unique. And that’s going to be something that’s going to have longevity.

David Nilssen  12:36 

Yeah, no, I was that the original thesis from the get-go that data and AI, or is that evolved as well?

Raazi Imam  12:42 

No, that was the original thesis from the very beginning, because we wanted to invest in really, really top tier CEOs data. And then the third piece, which we stuck to, as well as we like investing in markets, where we have some Ottawa call it an unfair advantage. In other words, we have a really good understanding of the entrepreneurs, we have a good understanding with the other partners, for example, in educational institutions, startups, incubators. And so for us, those two markets are really Seattle and LA. We know those markets pretty well exclusively.

David Nilssen  13:14 

Are you able to share any of the companies that you’ve invested in or some of the outcomes that you’re excited about in the portfolio?

Raazi Imam  13:20 

Yeah, we’ve had five exits so far. I’ll share one, we had a company just a few months ago, that will, actually, I can’t probably share that one. Because the deal hasn’t totally closed. But I’ll share an example of a company that we really like that we just invested in and fun to, we invested in a company called Unreal Labs, which is think eSports meets crypto meets blockchain. They’re building a really world-class game. And the founder is a former head of Microsoft ventures, and a longtime crypto gamer himself. And so in that situation, we’ve invested with some pretty, pretty big name, other institutional investors as well. So we’re excited about what these guys are doing and kind of where they’re taking our business.

David Nilssen  14:17 

Awesome. Tell me you were talking about this a second time. I think this is an interesting opportunity for us to talk a little bit about the other side, right? So you guys are typically the ones stroking the checks and deciding whether this is an investment that you want to move into. But being a startup founder sounds really sexy, but it is a lot of work because the individuals both chief cook and bottle washer, oftentimes moving into a market, they may have some expertise in but oftentimes just saw sort of an opportunity. But when you think about like looking at that startup founder, you made the comment that you’re a big part of the investment decision is on your belief that they’re going to be able to sort of figure it out. Like, are there any sort of attributes that you’ve seen for the startup founders that sort of help them be successful?

Raazi Imam  14:59 

Yeah, sure. significant depth in the space. Either they have it or people on their team have been an entrepreneur ideally in the past, so that they don’t have to make the same mistakes around people and operations and other things. Grit as an important characteristic we find, right, because they’re gonna have to pivot and make changes and adjust a really strong aptitude and sort of curiosity to learn, and consume information and pivot quickly. Really, really important characteristic. And for us, like these are things that either we are sort of measuring analytically, when we’re going through the diligence process, we’re also talking to their previous employers and other people in our network, possibly to understand if they’ve actually done that, and connect, it can be proven, because everybody interviews well, right, now we’re gonna go to an interview and tell you that they suck at anything, typically. So there’s a lot of data points that we’re kind of pulling together to sort of get that full view of that entrepreneur.

David Nilssen  16:03 

Is there anything that comes to mind when I ask you? I mean, the easy answer is obviously the inverse of some of these things that you’ve talked about. But what are the one or two things that you most commonly are reasons you most commonly would pass on investment and opportunity?

Raazi Imam  16:17 

One thing that gives us pause, I wouldn’t say we would necessarily pass one thing that gives us pause, we feel like the entrepreneur can’t raise money. And that’s one that probably if you’re not in the investment world wouldn’t realize, but like, do they have the ability, do they have that, you meet some people, and you just get a vibe and an energy and you connect, and there’s a level of comfort you get or a level of confidence that that individual builds in you. They don’t have that, it gives us some pause about whether we should make the investment irrespective of how amazing maybe the spaces or what the startup is doing. Because at the end of day, they’re the tip of the spear, they’re the ones that are the face of that business. And if they can’t close deals, and they can’t convince investors to buy or buy into their dream, like it’s going to be hard for us.

David Nilssen  17:04 

Yeah. And if you guys are precede are at the seed stage, you’re early in the transaction, right? A lot of the success of your future investment depends on their ability to bring on more capital and help scale faster, right?

Raazi Imam  17:14 

That’s right. And even though we will introduce them to later-stage funds, if they can’t close those deals, we’ve got a problem. So that’s an important thing we look at.

David Nilssen  17:25 

A few minutes ago, you alluded to the fact that you guys started the fund, because you wanted to play a more active role or be able to contribute value in different ways outside of providing capital, which is the obvious one, what are some of the things that you guys do to sort of help and bolster the success of your portfolio companies?

Raazi Imam  17:42 

Yeah, so there’s a certain amount of coaching and mentoring. So we have people on our team that will help with things like pitch decks and positioning in the market, those kinds of things. We get involved in helping close commercial deals quite a bit. So Andy, Sanjay, and I have a pretty good network, whether it’s in the enterprise space, or the media, or maybe just in the banking, and whatever it is, whatever the space is. So if we can help connect a startup entrepreneur to a company that they want, a buyer, or a service provider, whatever it is, we’ll do that. And sometimes it’s recruiting. We’ll help them with recruiting, recruiting the right talent, CRO, CIO, CEO, VP of Marketing, whatever it is, because all three of us come from being entrepreneurs, ourselves, we’re not the sit back and let them just do their thing. We’re like, what can we do to help you? Right? What can we do if we have to roll up our sleeves and get in there with you a little bit more? So we can help activate things or get them over a hump. Like we want to be involved in doing that.

David Nilssen  18:45 

Yeah. What about, on the flip side, so this is the way that you guys are contributing value. But if I was raising capital today, let’s hope that I’ve got more than one person who’s willing to invest in the business. Like if you were advising an entrepreneur, maybe you weren’t in the transaction. So your objective on this particular one, like what are the questions that they should be asking of potential investors to help them effectively choose a long-term partner?

Raazi Imam  19:10 

Yeah. So I think one of them is what you just asked about is some entrepreneurs don’t want investors to be very actively involved. Some of them do. Some entrepreneurs feel like they really know the space and they have an ecosystem. They just want the money. They just want money, capital, other entrepreneurs want a seat at the table from an investor or whether it’s a board seat or a board observer seat, there’s a bunch of different ways to do it. And so I think, if you’re an entrepreneur, like you need to be really thoughtful about who you’re bringing to the table. Sometimes investors are great investors, but they’re terrible board members. Sometimes they’re disengaged, sometimes they can just be frankly, downright rude and difficult. So I think that’s important also, certain funds and certain As members of those funds have access to certain commercial relationships and other things, too. So I think if I’m an entrepreneur, I really need to think about strategically what I need to help my business be successful. And what are the key elements to that? And who should I bring to the table? Whether it’s an angel investor, an institutional investor, whoever it is, helped me accomplish that.

David Nilssen  20:21 

Yeah, I think it’s a really important relationship. Speaking of which, your first business came in, you had a business partner. Now in this operation, you’ve got three of you, I should say, two business partners, like, what’s the key to making partnerships work, because the often people are watching businesses with somebody else. And that can be both. I’ve seen a lot of these erode over time. And I’ve seen some be very successful, what sort of the advice that you have?

Raazi Imam  20:46 

Yeah, I would say it’s transparency and communication. You and that individual start on a journey at the same time really aligned. And then over time, people’s interests and desires and direction changes. And if those two individuals are transparent, and communicate well, they can figure all that out. If they don’t, I think that’s where problems happen. Maybe the third thing is trust, which kind of comes from being transparent, having good communication, but I think that’s the difference. It’s been a journey for us too because Greg and I have known each other and work together for quite some time, Andy, Sanjay and I had known each other work together for quite some time. So we kind of had a chance to know how we are and what makes us strong and where our blind spots are. And I think as I’ve gotten older, and as they’ve gotten older to, like, there’s a lot less ego at the table. It’s more about being focused on the business. And in this case, in the fund business, it’s helping our entrepreneurs be successful. So that part’s nice. That part’s nice that there isn’t as much ego on the table. And we can really just sort of get past that and just focus on the actual business and doing the right things.

David Nilssen  21:54 

Yeah. And how do you guys divvy up your roles? Like, when you first started there, how did you think about, like, who’s going to drive what pieces of the business because my experience, also had partners, and every business I’ve done is, clarity makes a big difference?

Raazi Imam  22:07 

Yeah, and as you probably also know, David, like that changes. What you focus on depends on the stage of the business, what your strengths are, what the business needs, etc. So for the fund, for example Sanjay is in LA, Andy is in Seattle, I’m an SF. So I’ll give you an example. One of the things that is part of my charter being in San Francisco is building those relationships with these later-stage funds. So when our seed-stage companies are ready for an a round, or a B, round investment, I happen to sit in the market where there’s a thousand, A and B stage funds sitting here. So what am I doing to help our portfolio companies get access to that capital at the next round? And so that’s a good example of like, being in a certain location, and having a slightly different charter than the other two?

David Nilssen  22:58 

Yeah, that’s interesting. So you guys positioned yourself right outside of that sort of what I would call crowded space, which is your Series A, Series B, those types of organizations, you’re building relationships with them, so that in the future, you can help the entrepreneur gain access to their capital, but do you ever find that they’re also a referral source for deal flow because somebody comes to them too early, and they’re sending them upstream?

Raazi Imam  23:24 

That’s right. It works exactly that way, both directions. These A and B stage funds, sometimes entrepreneurs will come to them and be like, oh, you’re too early. Go talk to Unlock? Yeah, those are the guys that are investing in as a matter of fact, we also have an incubator as part of our thesis in our fund, which, we’re investing at not even the precede we’re investing in like the ideation stage sometimes, right? So we’ll have startup founders that are helping it even build a product with us. And we’re funding that just to see if that’s something we want to do and actually spin out into a company. So absolutely, these later-stage funds will definitely send us some interesting deals from time to time as well that we look at which helps us with our deal flow.

David Nilssen  24:08 

Very cool. I have to ask a selfish question, because I mentioned this as we started the podcast, my belief is that we’re sort of living through this fundamental transformation in the way that we work and live. And I talked about as a borderless mindset, but obviously I run a borderless talent business, the market is super, I should say the ability to access talent right now is a lot tighter than it has been historically. And that’s just evolving, as people are saying, oh, we’re going to work in an office. We’re not going to work in an office, we’re going to be a hybrid environment where an offshore, onshore, nearshore like how do you guys think about talent strategy inside your portfolio companies and how are you sort of helping them navigate this environment?

Raazi Imam  24:49 

Yeah, a couple of interesting trends I would say one, more and more the idea of having offshore engineering in offshore development is becoming a reality. And so if, as a matter of fact, I would say if, if engineering isn’t diversified, and there isn’t an offshore component to it, we feel like, our portfolio entrepreneurs aren’t thinking about it the right way, you want to have a hybrid model, engineering talent being local as well as offshore. So I think that’s important. One of the things that’s been challenging for us in sort of thinking borderless is when we’re actually evaluating these entrepreneurs, we like to meet with them in person, we like to go to their opposites. And that part’s been hard for us because we’ve invested through COVID, because we can’t do that. And so we’re kind of excited to be able to go back and do that. As a matter of fact, I was on a call this morning where we really liked this entrepreneur. But we’re not going to probably make an investment until we go visit with him directly in person face to face. And that’s sort of part of like I would say, Andy, Sanjay and I’s superpowers at Unlock is each of us brings our own experience to this conversation. And so we always leave with having gotten back different things from that entrepreneur and that team. And that helps us make, I think, a more balanced educated decision on whether we want to make that investment or not. So like the borderless thing is real and it’s happening, but then there’s also this, like, core fundamental, like, hey, we really need to meet with these people, before we read a million-dollar-plus check, and make sure we really understand who they are and what they’re about.

David Nilssen  26:28 

Yeah, it’s going to be interesting how it evolves over the next, call it two to three years, I think there’s been a lot of grace given to companies in a totally online environment, because COVID was happening. But now as that’s starting to come back to what I would call a more normal place, and people are getting called back into work, it’s going to be curious to see how that sort of all evolves. Because my experience has been that, from a productivity standpoint, being remote, it’s exceptional collaboration is the place where there’s still a lot of room for improvement. So be fun to see how that happens. Raazi, we’re getting to the end of our call here. But just last question for you is really, you’ve been an entrepreneur, and now you’re an investor, do you foresee a time where you might jump back in and say, I’m ready to get my hands dirty and I’m going to be that leading CEO again?

Raazi Imam  27:14 

I think about it all the time because we see these companies all the time. And all of us, like deep down in our core love growing and building businesses. It’s possible, I am not wanting to do it today. But I would never say never. Right? There might be the right opportunity at the right time with the right folks that I might jump back in and do another startup. It’s entirely possible. It’s in our DNA and like, feeds us, right. We love it. So probably.

David Nilssen  27:42 

Can’t take the entrepreneur out of the individual. I love it. Well, we’ve been talking to Raazi Imam, who’s a General Partner for Unlock Ventures. Raazi, if people want to learn more about you and what you do, where can they go?

Raazi Imam  27:52 

So you can go to or you can reach out to me as well at [email protected]. I’d be happy to talk to you.

David Nilssen  28:00 

Awesome. All right. Well, thanks for being on the show.

Raazi Imam  28:02 

Yeah, thank you, David, for having me. It was awesome talking to you. And best of luck to you on the podcast.

David Nilssen  28:07 

Thank you.

Outro  28:10 

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