Neil Patel

I hope you enjoy reading this blog post.

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Troy Pospisil is the cofounder and CEO of Ontra which is a provider of technology and services for contract automation and intelligence. The company has raised $250 million from investors like Battery Ventures and Blackstone Group.

In this episode, you will learn:

  • Fundraising
  • How Ontra is solving this big problem
  • Troy’s top advice before starting a company
  • Why consulting or private equity gives you an edge in entrepreneurship


This episode is sponsored by Zencastr, my #1 podcast tool. They provide a crystal clear sound and gorgeous HD video. What I love about it is that it records separate audio and video tracks for me and the guests. Plus there is a secured cloud backup, so you never lose your interviews. It is super easy to use and there is nothing to download. My guests just click on the link and w start recording. Go to Zencastr and get 30% off your first three months with a PRO account.

This episode is also sponsored by Vinovest which is a company that allows accessible and affordable investing in fine wines, an investment that is less volatile and often more lucrative than investing in traditional stocks. Go to their site and receive 2 months of fee-free investing. Be sure to mention that the DealMakers podcast is helping you to same on 2 months of management fees.

For a winning deck, take a look at the pitch deck template created by Silicon Valley legend, Peter Thiel (see it here) that I recently covered. Thiel was the first angel investor in Facebook with a $500K check that turned into more than $1 billion in cash.

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The Ultimate Guide To Pitch Decks

Moreover, I also provided a commentary on a pitch deck from an Uber competitor that has raised over $400 million (see it here).

Remember to unlock for free the pitch deck template that is being used by founders around the world to raise millions below.

About Troy Pospisil:

Troy Pospisil, is founder and CEO of InCloudCounsel. Troy oversees efforts to scale up the legal technology company, bringing its global, end-to-end solution for negotiating and managing routine legal work to some of the world’s leading companies. In just four years, Troy and his diverse team of software and machine learning engineers, ex-corporate attorneys, and financial services professionals are now delivering InCloudCounsel’s solution to hundreds of companies around the world. Prior to founding InCloudCounsel in 2014, Troy worked in private equity at H.I.G. capital and in management consulting at Monitor Deloitte.

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Connect with Troy Pospisil:

Read the Full Transcription of the Interview:

Hey, guys. Today’s episode is brought to you by Zencastr. I remember back in the day when I was looking at putting together Zencastr. I was looking for a solution that would help me in putting things together. Essentially, this is what allowed me to bring DealMakers to life. Basically, Zencastr, what it is is an all-in-one solution where you just send a link to the person that you’re looking to interview. They would plug in their computer with their video, with the audio, and then you are good to go. You would piece everything together, give it to your audio engineer or even edit it yourself, and you are off to the races. Now, if you’re looking at getting into podcasting, you should definitely check Zencastr out, and you could also get a 30% discount, and this is the discount code that you will be able to redeem by going to Lastly, I was very much blown away when I found out that investing in wine has been one of the best-kept secrets amongst the ultra-wealthy. This is now not the case anymore. I came across this solution, which is called VinoVest, and they are a great solution that allows you to diversify investing by implementing or including wines into your portfolio. Take a look at this: wine has one-third of the volatility of the stock market, and yet it has outperformed the global equities market over the past 30 years with 10.6% annualized revenues. It’s a really good way to diversify your portfolio, and you could also get two months of free investing by just going to, and by going there, you will be able to redeem your discount.
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Alejandro: Already hello everyone and welcome to the dealmakerr show. So super excited with our guest today I mean we have an entrepreneur here that you know has has done it. You know building scaling financing crazy serious bees. Of hundreds of millions I mean you name it and also building businesses even in ninth grade. So I think that we’re going to enjoy the conversation with this founder but without furtherther ado let’s welcome our guest today Troy Pospisil: post piil welcome to the show. Thanks.

Troy Pospisil: Ah, hundred great to be here. Thank you for having me.

Alejandro: So originally born. Ah in Southern California where the good weather is so tell us about your upbringings especially with your Hustler Hustler you know little businesses that you had going on.

Troy Pospisil: Yeah, absolutely well I was very lucky and fortunate to be born in Southern California I didn’t know that other people shoveled snow out of their driveway until pretty late in life I was very fortunate to have a loving family 2 loving parents who were. Still married which seems to be an anomaly these days and loving grandparents who lived by us and were a big part of our upbringing and 2 brothers who are awesome people and I’m still really close with but I got really interested in business and entrepreneurship and just working. In general very early in life I had a couple of jobs that I got really early I got a job at a clothing store actually at a surf shop for a summer which I thought sounded pretty cool but ended up just being folding clothes after people came through and tore the place apart. Trying on clothes and moving things around the store and then I thought it would be interesting to see a professional environment so at a pretty young age got a job at a local law firm in the file room I don’t think this is ah a concept anymore. But I would file physical papers in a file room and retrieve them. When people were requesting information but both of those experiences taught me that I should probably try and make sure I got good grades so I could go to college and didn’t have to have a job that was really repetitive wanted something more interesting and stimulating and a bit more creative. And then got the idea early that being an entrepreneur would be really interesting and exciting. So my first economic journey that I started on to call it a business would be a bit generous but a scheme is probably a better word was I poked around the internet and I found someone in actually China who. Was willing to sell me fake Louis Vuton Handbags and I took my savings and I imported about $1400 of Louis Vuitton Handbags or fake louisvaton handbags that I should say and I I lived in Orange County where people wanted these things and I started. Selling them and my my best sales strategy is I would set up in the break room at offices law firm offices. You know, consulting firm accounting firm offices and ask the office manager to email everyone in the office to come and look at my wares and in an hour. I would make a couple thousand bucks as a 14 year old which was pretty spectacular I did this for a full summer and then got a call from a prospective customer to meet them in a parking lot which as bizarre as it was wasn’t it wasn’t that strange for my business. It was sort of a word of mouth business.

Troy Pospisil: And there was a sting operation I got surrounded by about 5 people working for a private investigation firm working for Lvmh. They were curious. Why I wasn’t in school which was a good question given that the school year had started I think my tenth grade year had started and so that was the end of of my criminal enterprise. Ah, yeah I had a couple another couple other interesting experiences but I’ll mention one that was a good learning experience I somehow about a year later the following summer got in touch with someone who was associated with a clothing company called baby fat I don’t know if any of your listeners will. Remember that. But it’s the women’s line of fat farm which maybe is something people are more familiar with and they were trying to figure out a way to offload last season’s clothing that was still sitting in the warehouse. And they were trying to be a more upscale line for their category and so I think they had some agreements with some of their retailers that they couldn’t sell into the traditional channels like Ross and burlington coat factory but they could sell it to me I was not contractually part of that contract and so. Were willing to sell it to me at 75% off their list price and I set up a booth at the local fairgrounds. There was what we called a swap meet or sort of a ad hoc marketplace that would get set up at the local fairgrounds in Orange County and I would wake up at 5 in the morning I did this with a buddy of mine we would drive over there. We bought like a big beach tent type thing and some racks of clothing and we would set up and we would stand there. All day was long days just standing around haggling with customers trying to tell them why this pair of baby fat beans or baby Chet. That t-shirt was the thing for them and we would do great in a weekend I’d make a few thousand dollars as a fifteen sixteen year old so that was another great experience just learning about hard work learning about sales learning about haggling learning about pricing and margins and. If I gave a discount what would that do to my margins at ah at a pretty young age so that was a great experience and I did a a couple other funny things. But I’ll I’ll skip over all the little schemes I came up with in high school but ended up going to. And why you for college after I finished high school was really lucky to get accepted there and be able to go to New York

Alejandro: Now now before we we talk about New York and also the the experience that you had there working for this pet company as well. What do you think triggered you to really enjoy so much the business world and. And the entrepreneurial world I mean was there like a specific moment or is it all I really love this thing.

Troy Pospisil: I think part of it was the experience of having ah jobs at the clothing store in the lawfront that I didn’t particularly enjoy and realizing that maybe having a job wasn’t the thing for me, you know I was also just lucky enough to be born where I was born. Orange County is a pretty entrepreneurial place and I had a number of good friends whose families were entrepreneurs and you know I got exposed to that as a potential career option and was just really attracted to it. You know. It seemed like you could be creative come up with your own ideas create products create businesses out of those ideas versus just being 1 thing for your whole life. Um, and just being sort of. In ah in a particular swimline for your whole career I liked the idea of the creativity and the variety and just being able to come up with ideas and go go make them happen.

Alejandro: Nice. So then let’s talk about making things happen because when you were in and niu you started working. You took this gig with um with a pett food company that was looking to expand in the East Coast and one of the things that you did was just say fill up a shuffle block a shuffle back and. And then go around you know a hundred stores knocking door to door to see if they would you know enroll you know with the with the company. So I guess my question there is what did you learn about sales and about knocking on every door that you could in order to really get you know business done and.

Troy Pospisil: Yeah, that a great question. So just to give a little bit of background so I was at and Nyu I you know wanted some spending money and I wanted to help pay for my tuition I had a lot of friends that were getting jobs at coffee shops or restaurants and you know I thought back to my time. Selling and thought you know there’s there’s probably a better way to make more money in the same amount of time that you would get paid hourly busing tables or pouring coffee or or whatnot and so I got an opportunity with a pet company that sold pet that manufactured and sold pet treats or dog food primarily. It’s a California company that was sort of early on creating organic dog food and they were trying to open in the new york market they had set up a relationship with the distributor but they needed to have a salesperson on the ground actually go talk to store owners and convince them to carry the product. So I got a job as a contractor doing that. Distributor gave me a list of all of the stores that they had on their delivery route in Manhattan and that was about one hundred and fifteen stores and I literally had a duffel bag with sample products so I had bags of all these different types of dog treats and I went door to door. And I would walk in to the pet store. So I have been to every pet store in Manhattan at least as of you know, fifteen plus years ago I’m sure there’s been a lot of turnover since then but I I went door to door and I took I got a subway card I got a you know monthly subway pass. And I literally wore through the leather of my shoes I know that’s sort of an expression but I literally wore through my shoe leather trouncing around New York and I would walk in I’d say can I speak to the manager can I speak to the owner and I would give them my pitch which was a very basic pitch. You know these are organic. They’re all natural. And the meat is high quality. It’s a great price and if there were dogs walking around the store I would open up a bag and give them the tree look how much the dog likekes it. You know in hindsight not a very complicated sale that these folks have shelf space to fill. They’re not super averse to try new things so I was very successful in getting most folks to fill in order. But. You know, ah just a lot of good learnings not being scared to walk in asked to speak to the decision maker getting comfortable making your pitch hitting on the different points of value. You know to to a somewhat small extent trying to read the room understanding which points of your pitch are going to resonate. The person you’re selling to you know, selling to a really highend pet boutique and Tribeca is really different than what a store owner in Morningside Heights cares about I had sort of a funny experience where I started talking to this 1 owner in a rougher neighborhood. Um and the northern end of Manhattan.

Troy Pospisil: And was telling him about my organic dog treats and you know he sort of like I’m I’m not sure my customers care about that. He’s like mostly what I sell are spike dog collars and I’m just trying not to get robbed and I was like what do you mean and he literally takes a shotgun from under the counter pulls it out and puts it on the table and he’s like this is what I mean.

Alejandro: Ah.

Troy Pospisil: I Think the customer you’re targeting is different than than who I’m serving and the types of products that people are looking for when they come in my store. Ah, but just a great experience in not being scared to go knock on doors. And pitch your product and hear what the customer has to say firsthand.

Alejandro: That’s how amazing now in this case for you I mean after completing your studies at Nyu and then also studying in China where you know you also had your gig there with with one of your friends that you ended up selling. Basically what happened is that you went into corporate I mean that’s something that that I’m a little bit. Surprised by because here you are super super entrepreneurial. You know type of driven. So why did you go into corporate instead of like maybe like launching your own thing right? away.


Troy Pospisil: Yeah, it’s a great question and I’ll I’ll start by saying I’m really glad that I did I learned a lot in the years that I spent being a management consultant and working in private equity. But at the long and short of is I had a handful of professors that I really respected. And had built good relationships with who were older and wiser than I was and and Ny is a really special school in in the in the economics and business departments. You have a lot of professors who have real working experience and maybe teach part-time but are working at banks or you know working in industry so you get a really realw world perspective. From the teaching staff there and I’ve got the advice look what you’re doing is super interesting. But if you really want to you know make it big. You really want to learn how large companies operate you want to build a network within corporate America and gain some of those skills. And go through those training programs that other people are basically going to pay you to train you ah so I took that seriously and I went through the interview process and was lucky enough to get a job in management consulting where I spent the first two years of my career.

Alejandro: Now you know one thing that is very interesting is you did management consulting and then you did private equity and some of the um, a based entrepreneurs that I get to interview is people that either have experience on investment banking or in consulting or on private equity or let’s say Vc. So out of those 3 you have 2 of them. So I mean you, you’re a very dangerous entrepreneur I would say.

Troy Pospisil: Um, I’ll depend it depends who you ask, but those are great experiences early in your career. You know in both of those experiences you get to see so many different companies get exposed to various industries a lot of different business models. To work with a lot of different people that have different skills that can train you on what they know you can learn from them. You know in in consulting you’re going from project team to project team I worked on projects for Toshiba Toyota Nike Life Technologies and so just seeing really scaled problems for big. Companies that are the the big players in their industries and working on cost savings initiatives operations problems, big technology implementations m and a integrations that was all in my consulting life. So you just learn a lot really really quickly and you gain. You know the basic skills you need as a business professional how to solve problems with data how to analyze that data in excel how to summarize and present the key points to decision makers how to gather information from stakeholders. Um, so there’s just a lot of good raw skills that are very relevant to. Being a business leader as an entrepreneur or you know working at a company and private equity sort of more of the same working really really long hours on a lot of planes but getting the opportunity to work with really smart people on really complicated interesting issues across a bunch of different industries. Getting to meet a lot of different really interesting entrepreneurs and in private equity in particular starting to think hard about how do you finance a business How do you think about investing in different business editives the return that you’re going to get on those investments do that analysis accurately. And I think in particular as an investor starting to think really hard about business models. What’s a good business There’s a very big difference between a good idea or a good product and a good business and so just and I was I was again very lucky to have landed at a firm called Hig Capital which couldn’t have more respect for that firm. Really really smart people the way they invest is really interesting and it was awesome to be exposed to and some of my best friends today are people I met at at both the consulting firm and the private equity firm.

Alejandro: So so so talking about why you just sit there. What is the difference between a good idea and a good business.

Troy Pospisil: Ah, that’s a great question so you know a good idea or a good product is is necessary but not sufficient to build a good business ultimately a good business has to have good economics and the 2 key economic. Things that I would look at now as an investor if I was evaluating ideas as an entrepreneur are the margin profile of the product you’re selling. You know, can you sell the product for more than it costs you to create the product and then the customer acquisition cost. You know that’s something that I think a lot of entrepreneurs fail to think about is can you scale the business in in ah in an efficient way with capital so can you acquire customers and are you going to get enough in terms of the lifetime value of what you’re selling those customers. To make that a sustainable business and you know as as a very real time example, the changes that Apple just made to the data that they’re willing to provide to users or advertisers on the Facebook platform has really changed the economics of customer acquisition. For a lot of consumer tech businesses and so it’s totally changed the math and made a lot of businesses that previously were sustainable that had reasonable economics in terms of their customer acquisition cost relative to the lifetime value of the customers are acquired and and and now they can’t make that math work. So a lot of these consumer apps and I won’t name any names are great products people buy them. They use them. They love them. But now that their customer acquisition cost is so much higher on a per user basis. They’re no longer good businesses and so it’s ah it’s just ah, especially as an investor you learn, really really quickly. That there’s a big difference between a good product and a good business and then there’s an investor. Additionally, a really important foundational learning is there’s a really big difference and sort of the same morning but there’s a big difference between a good business and a good deal. And a good investment. You can have the best business and overpay on valuation and that that can be that will end up being a bad deal and you can make money as an investor investing in subpar businesses for the right price. There’s you know there’s It’s not always true. But for the most part there’s and there’s a fair price for almost any asset.

Alejandro: So then let’s talk about good businesses. Let’s talk about a business called Entra that I think you know very well you know, let’s talk about your baby. Let’s talk about entra. So so tell us about you know the the when enttra you know came knocking. You know as an idea and how you went you know about executing because. You know I’m sure at the hig you were making a good living and you know taking a haircut you know on the income side and and taking a dive you know and the leap of faith was probably not an easy one. You know to to take on so so walk us through that through that process.

Troy Pospisil: Yeah, ah, absolutely well maybe I’ll talk about the idea first and if you’re interested and I can talk about my personal decision making process on’m taking that leap if if you want to chat about that. So.

Alejandro: Grape.

Troy Pospisil: You know I was an investment professional at hig and I was inspired to start entre based on 2 problems I experienced in my personal life as a professional. So the first was high volume routine contracting so as a big business especially in financial services. We had a really high volume of. Routine contracts that were part of our day-to-day life. So these are contracts that are 5 ish pages that we have to review negotiate lightly execute and then ideally keep track of what we agreed to and this was happening literally thousands of times a year across our organization across various contract types. Non-disclosure agreements. Non-reliance letters vendor contracts engagement letters and it was really time consuming. It had to be done well ideally it was done consistently and ideally we would keep track of everything we agreed to so we could easily answer questions that implicated. Requiring data from across agreements like where do we have active nonsolicits in place. So like what are all the companies where we can’t currently actively solicit potential employees from um and that was ah that was a problem and it was a really time consuming problem and I again I was very lucky to live in San Francisco I had a lot of really good friends. Working in enterprise software in product in sales in engineering and it was just thinking a lot about technology and it seemed like an an interesting problem and 1 where if you combined technology with an alternative labor model. But you were starting to see pop up with the likes of companies like uber that you could create a product that was faster higher quality lower cost and really created more value because you digitized the workflow which gives you the opportunity to capture a lot more data the second problem that I dealt with on a day-to-day basis. Which we also solve as a business is keeping track of information in really complex corporate contracts. So as an m and a professional you’re dealing with purchase agreements credit agreements operate in agreements and among a long list of others like leases and employment contracts. But it’s. Very often many many times a day you’re asking yourself gosh. What did we agree to in that contract. What is our when is our reporting requirement What did we agree to in that reporting requirement you know in this type of agreement with this type of counterparty. What have other people in my organization. Agree to in the past on these really key terms and we we weren’t able to do that because the state of affairs for most businesses is that they spend a lot of money and time negotiating complex contracts. They execute them. It becomes a pdf and then you know ideally they save it.

Troy Pospisil: On a shared drive somewhere where everyone has access to it. But even that’s generally not the case and so I I saw that and thought you know again, this is a really interesting problem where software could be really valuable taking complex corporate contracts turning them into structured data and then delivering. Ah, digital workflow tools around that data so that you could proactively and easily manage your affirmative obligations in all of your important agreements with your important counterparties easily reference your restrictions across all of your agreements and easily benchmark across all of the contracts within your organization. Which if you do that in an organized structured fashion becomes a real asset and a real strategic advantage for your company because you can negotiate more effectively on your most important agreements which have real economic implications for your company.

Alejandro: Now Yeah I mean that’s a lot I get so so now now that we understand you know and that you kind of like walked us through the problems that you were seeing and how to really tailor a solution perhaps Tailor a solution that would address that.

Troy Pospisil: So I’ll pause I’ll pause there and see if that made any sense.

Alejandro: Why did you decide to take the leap of faith with this.

Troy Pospisil: Yes, I’ll talk ah a little bit about my personal journey. You know first and foremost I thought I really wanted to go back to being an entrepreneur you know I took the advice of my mentors and I got great experience. I had built. Ah what I think is a really good network I had. And now a lot of good friends from you know that I built in consulting and private equity. You know I didn’t you know I was still relatively young, but I’d I’d learned enough that I felt confident that I could go out on my own and with the help of my network sort of figure it out. Um, I had the the sort of raw skills that I’d wanted to develop working for sophisticated institutions and I was you know I was in my late twenty s I didn’t have a mortgage I was engaged but not yet married. Was really frugal in my life and I thought saving was really important if I wanted to be an entrepreneur one day that’s a piece of advice I don’t hear a lot of people give entrepreneurs but save ah when you’re working because that’s going to give you that window of ah time where you can go take a chance. Not take a salary for some number of years and you know a lot of people give entrepreneurs the advice that just stop spending money move into your parents basement eat ramen noodles. You know I think that that can be a solution to taking a leap of faith I think ideally you want to stay engaged with your network socially because your network. Especially when you’re starting an enterprise business selling b two b can be really really valuable and so you know I I saved enough money that I was able to continue spending time socially with the people on my network. My fiancee now wife at the time I was also very fortunate had a really stable job and so we sort of made a decision as a. As you know, ah a family to be that it was an okay risk for us to take for me to step off and not take a salary for some indeterminate period of time I had savings she had a really stable job as a corporate lawyer and I could take a few years and you know take a big swing. Ah and I just knew for me personally having had a couple entrepreneurial experiences having thought thinking for years about trying to get back to being an entrepreneur that if I didn’t take this chance I would really regret it I had a great job. A really economic. Ah, you know it was a. Was I was getting paid. Well it was really interesting if there’s if there’s any job to have working in Middle Market Private equity is super fun and interesting. Um, but I just knew if I didn’t take that leap that I I would really regret it and there was no better time for me to do that? No mortgage. No kids.

Troy Pospisil: Teed myself up with savings and I was young but I you know again I felt like I learned ah a little bit and enough to hopefully be able to figure out the challenges that would no doubt present themselves.

Alejandro: Now talking about ontra here So taking the leap of faith you go at it. How do you guys make money I don’t try.

Troy Pospisil: So we were an enterprise business were b two b so we have 2 core businesses First is what we call contract automation so we partner with large organizations to take over their high volume routine contracting. As ah as a full stop global solution so they have high volume routine contracts. They need them marked up negotiated and ideally turned into structured data so that they can do benchmarking or reporting against what they agreed to in those contracts they want it done at a high consistent quality. They really care about speed. Um, and and ideally the costs they want to save money from any of the potential alternatives and so that’s the solution that we deliver to those to those companies you know blackstone is you know is 1 of our investors. They were a big customer prior to becoming an investor or a global organization. They have. You know 10000 plus high volume routine contracts that they have to process as part of various business processes every year and they need a solution for getting that done quickly cost effectively and a high consistent quality on a global basis. Um, and so we’re we’re a consumption-based pricing model. We charge on a flat fee per contract basis.

Alejandro: And and and.

Alejandro: And I was going to ask you I mean black blackstone Also a big investor here I mean how much capital have you guys raised to date.

Troy Pospisil: And it’s literally that simple for the customer.

Troy Pospisil: We’ve raisedd about two hundred and fifty million dollars over two rounds of financing so we did our our first. Ah you me to go through the whole journey I can talk about our friends and family.

Alejandro: Yeah I think that broadly what it’s going to be very interesting here is especially the decision of bootstrapping the business for a little bit longer. So.

Troy Pospisil: Yeah, absolutely um I’ll sort of joke a little bit. You know I came from private equity where we valued businesses primarily based on eba daw or ebit if they had a big capex component and I was came from the school of thought that a business was supposed to generate cash flow. Um I hadn’t really been exposed in my career to this world of ah you know businesses being valued primarily on revenue growth. You know being valued for the underlying technology that they developed sort of ah to me it was sort of all cash flow I was from the school of thought of Warren Buffett Seth Carmen Howard Marks that was sort of my professional world and so when I set out to build a business I was sort of modeling it on the the type of success that I’d seen businesses achieve which is building a business that achieves some level of scale. Good consistent growth. But you know. Some level of profitability so that it could stand on its own two feet and we started down that path when we started the business. We did need some startup capital which was which was really helpful. We raised from about 30 of our friends and family that was great because we engaged our network and. Engage them in a way that they didn’t just want to see us succeed because they cared about us. But now they had sort of an economic incentive to see us succeed so we raised from a lot of people that were in the industries that we thought were going to be really helpful to us in terms of as we started to sell our product and then we sort of. Ran lean for 5 years and there are no doubt pros and cons ah from that experience that I could talk about forever but at a high level running lean makes you really disciplined in the early days. You’ve got to have unit economics that makes sense. You can’t get too far over your skis on that. Ah. And you get really creative when you on sales and marketing strategies on you know, scaling resources you need for any function within your business. We I mean we were watching every single penny and that that was a good that was a good bedrock. For making sure that we sort of built the business and the culture around making sure that we were you know relatively frugal and so we did the friends and family that was sub $1000000 and then we sort of built a business for 5 years and we more or less ran it broke break. Even. Had good strong consistent growth. We tried to invest in growth and we came up with really creative ways to do sales and marketing in large part. It was me sleeping on friends couches flying all over the world for 5 years running myself ragged.

Troy Pospisil: But and then we got it done and then you know we built a lot of technology and without really realizing it. We sort of were a high-growth tech company that wasn’t how we thought about it that wasn’t what we set out to do but our numbers and the amount of software that we built and the the value that we were delivering to our customers. Ah. Resulting in a number of technology investors starting to reach out and that’s sort of when I became a little bit more wise to the idea that technology investors are really focused on revenue growth. You know the smarter technology investors are still really disciplined about unit economics and looking at your customer acquisition costs relative to the lifetime value of your customers. But if you’re investing intelligently in randd and in customer acquisition that’s going to have a decent payback. It’s okay to have negative mard negative net margins or negative e. But so that was an that was an interesting sort of learning for me and development in my professional career and we you know we talked to a handful of technology investors. And we were fortunate enough to partner with battery ventures and we partnered with 2 folks there Chelsea Stoner and Paul Morrissey both of which joined our board and they were a great partner and so they did a $ 40,000,000 round and that was our series. We called it. Our series a because it was our first institutional capital but we’d been. As I mentioned in business for 5 years and we’re a decent size business at that point.

Alejandro: So nice and then obviously Blackstone and and and there you have you know? um, incredible rocket ship that you’re writing now anything that you could share in terms of like the size of the business number of employees or anything else.

Troy Pospisil: Yeah, absolutely you know I prefer not to share revenue not to be too coy. But you know we’re our revenue warrants the $200000000 the Blackstone recently invested in the business were coming up on 250 employees right? now that’s a global team so we’ve got people in the us Europe and Asia. And we’re hiring aggressively. So if you’re a smart talented kind curious person. We’re hiring across functions randd sales account management. We’d love to talk to you.

Alejandro: And amazing now 1 question to to finish off here that I’d like to ask you here. Troy Pospisil: is imagine if I put you into a time machine and I bring you back in time to that time you know years ago where you were you know thinking about maybe making that leap of faith. From hig the company that you were working at and and you had the opportunity of having a sit down with that younger self and you were able to give that younger self one piece of advice before launching the company. What would that be and why given what you know now.

Troy Pospisil: Um, ah you know don’t be so hard on yourself. I’m my own worst critic which isn’t super healthy all the time. But um, you know, take time to appreciate. You know, savor the moment savor the wins celebrate more for yourself celebrate more with your team I’m impatient I’m always you know it doesn’t matter what just happened how big the win was my instinct is what’s next What’s next What’s next you know how else can we improve. What’s the next customer we can add what’s the next hire we can make and I’m very focused on the here and now and what ah what is the next step to drive forward in almost an irrationable insatiable way which is can be great. Um, but can be a bit can be a bit wearing on yourself and your team. So just you know. Have fun. This has been a really really fun 8 years I’ve been super fortunate. Our team is awesome I’ve been really lucky to build a great to help be a part of building a great culture and a great team I have a ton of respect and learn from the people I work with every single day I love. Being in the enterprise because we sell to really sophisticated challenging customers which to me is really fun to sell the the most sophisticated demanding customers in the world and just to you know, keep keep the pressure on work hard always think about continuous improvement across everything you’re doing. But. You know, just every once in a while take a step back appreciate it relax a little bit and and have fun because it’s short I’ve been you know I’ve been on this journey for 8 years with Entra. It feels like yesterday that me and my two co-founders were working out of the dining room. And my apartment in Russian Hill in San Francisco so it goes it goes by fast. Um, and so just have fun.

Alejandro: So amazing now for the people that are listening Troy Pospisil: what is the best way for them to reach out and say hi.

Troy Pospisil: Ah, yeah, great question. You can find us at Http:// So you know please check us out on our website if you want to reach me reach out to me on Linkedin I’m I’m pretty active on Linkedin. That’s probably the easiest way. To find me I’m not I hate to admit I’m not really on Twitter or Instagram or Facebook but I am on Linkedin.

Alejandro: So amazing. Well hey Troy Pospisil: thank you so much for being on the dealmakerr show today.

Troy Pospisil: Yeah, thank you for having me This was a lot of fun and it was fun to walk down some old memories.


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