Neil Patel

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Having begun his career at Siemens Healthcare, Carlos Reines went on to head a division of Spain’s leading telecoms operator Telefónica as a telecommunications engineer. But he was keen to re-route to healthcare and so undertook an MBA at Harvard, where it became clear where his future lay. In a new episode of the DealMakers podcast Carlos Reines shares the journey and the struggles involved with raising capital as a founder in a regulated industry for his company, RubiconMD.

The company that Carlos Reines has gone out to build includes top tier investors such as Waterline Ventures, HLM Venture Partners, or Optum Ventures. During this episode, listeners will gain access to how the process of fundraising changes as a company matures and moves from Seed to Series B and beyond.

In this episode you will learn:

  • How to navigate the ups and downs of fundraising
  • Ways to keep investors engaged
  • The due diligence process
  • Do‘s and don‘ts when dealing with investors
  • Off market clauses that investors may introduce in subscription agreements
  • Operating in a regulated industry and raising money


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 Carlos Reines:

Carlos Reines is one of the cofounders at RubiconMD. The company was founded in 2013 with a driving vision of democratizing medical expertise so that providers can offer every patient the care they deserve.

Originally from Spain, Carlos Reines is passionate about leveraging technology to drive change in healthcare.

Prior to RubiconMD, Carlos Reines led a division at Telefonica, one of the largest telecom companies in the world. Carlos Reines began his career at Siemens Healthcare.

Carlos Reines earned Masters’ in both Bioengineering and Telecom Management in Madrid, and an MBA from Harvard.

Connect with Carlos Reines:

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Intro music playing….   

Female:            Welcome back to the DealMakers Podcast Show with serial entrepreneur, Alejandro Cremades, bestselling aunnnnnnnthor of The Art of Startup Fundraising and cofounder at Panthera Advisors. In this podcast, we ask our guest about their successful acquisitions and financing rounds.

Alejandro:        Alright. Hello, everyone. So welcome to DealMakers. So today, I have a very special guest who I consider as well a good friend. Carlos Reines is one of the cofounders behind Rubicon and it’s one of the leading companies right now in the healthcare space, so I was very excited to have Carlos. Carlos, welcome on board here.

Carlos Reines:             Thank you very much, Alejandro. Very excited to be part of this.

Alejandro:        So tell me how you got started with the company.

Carlos Reines:             Sure. So I guess I’ll start by saying I’ve always been super passionate about this topic of technology applied to healthcare. I went through some tough family experiences which helped me understand the impact that someone can have over a person’s quality of life through technology and intervention, and I’ve been following this path. I went on to becoming a biomedical engineer, working health IT for a few years. And then it was really in 2012 I was in Boston for business school and I started going to a lot of entrepreneurship events. And in one of those, I met my cofounder. It was March of 2013 when we met. It was at a hackathon at MIT. It was called Hack in Medicine. And my cofounder Gil Addo was pitching the idea and this was right in line with the work I had been doing around technology applied to healthcare and improving access for patients. And we started, we met over that weekend, worked through the weekend, had a follow up meeting shortly after that and did another startup weekend a month later where we won best pitch and that sort of pointed me in this direction where I was in the middle of recruiting for a summer internship, cancelled everything, moved to New York that summer and started working together and that’s how we got started.

Alejandro:        Nice. So you were actually working on this while you were still in business school. So where did you get hours to be able to do something about this because I mean it’s quite demanding when you go to one of these Ivy League schools?

Carlos Reines:             Yeah, it was very hard. We started through first year and I continued doing it through the second year of business school and I would go to class every morning always under prepared because I had never read my cases or done all the homework, and then I would spend the entire afternoon working on the business to find myself almost every day at midnight having to read cases and prep for the following day. Some days I would drive from Boston to New York to meet with an investor. We were in the process of raising our seed round at the time. It was very tough. I remember when we were graduating from school and everybody was sad that they had to go back to real life, go back to work. I was the happiest person because I could finally focus on the business 100%.

Alejandro:        That’s amazing. I still remember those early days you know when we met I think it was back in 2014, no, or 2013 when you guys were getting started and just out of school. I mean it’s amazing how time flies and the accomplishments that you guys have been able to get so yeah, kudos to that. So I guess when you were meeting your cofounder in this case like what led you to believe that that was going to be a good marriage? I mean were there like certain qualities that he had that you thought that could really make this journey be you know like more interesting or what was there when you initially thought about potentially going at it with your cofounder?

Carlos Reines:             I think it was a process so met that weekend over that hackathon and we actually worked pretty well together over those few days and then we had a couple of follow up sessions. I remember one of those early sessions, we went to grab dinner with each other and we both brought our significant other to the dinner and it was this mutual vetting of each other, trying to get to know each other. We used to say that we dated for a while before things got serious. We had to go away from that analogy because people thought we were really dating. But it was a process where we’re getting to know each other, trying to understand what are our working styles, what’s our commitment. Is this person—will it be easy to work with this person? Are we aligned on the vision? Do we share the same values? Do we—are we committed to start doing this, and you know for any foreseeable future, go unpaid, go through the challenges and everything? I guess we’re incredibly lucky to have found each other at a hackathon because there are two things that are pretty interesting: one is that we share very similar background. We’re both biomedical engineers and we both graduated from business school but we have very different styles, very complimentary and I think I like the way Gil’s wife puts it. She says that she’s never seen two people disagree in a way that’s more constructive than what we do. And I think five years in to the business, I’m incredibly thankful that we got to meet each other because we have a really good working relationship.

Alejandro:        That’s fantastic. That’s fantastic. So talking about the business itself, so how has the business I would say evolve over time I mean from that initial concept that you had and what is the business today?

Carlos Reines:             So the business in simple terms, it is a platform that allows primary care providers to submit consoles to top specialists across the country whenever they have a question on a difficult case and they hear back within a few hours and based on that input from the specialist, the primary care provider can make much more important decisions on their patient’s diagnosis or treatment plan. And it really started off as a solution for providers. There are many, many tech platforms that are patient facing, all these tele-medicine applications but there’s almost nobody doing innovation for primary care providers so that’s the niche that we took on. And five years later, the business is still the same, connecting primary care providers to specialist. I think a lot of the tweaks that we’ve had to do to the model are around the complexity of rolling this out in a market that’s incredibly complex and incredibly fragmented where in most of the situations, the primary user of technology, the primary care provider, it’s not the payor because the insurance companies are typically the ones that hold financial at-risk for the total cost of care for the patients. So we’d have to navigate that say set where it’s B to B business with the third party and then you have to do an engagement with the clinic which is again a B to B type of relationship. And then you need to bring the clinicians on board which are our end users.

Alejandro:        Got it. Got it. And just like out of curiosity like for those that are listening now and you know that are also dealing with what could be you know sale cycles that are a little bit more on the longer end, I mean what kind of tip would you have for them?

Carlos Reines:             Yeah, it’s a very good question and I think that in particular for health IT I think that’s the ultimate example of an industry with a really long sale cycle and the larger the organization the longer the sale cycle. You need to have a lot of balls in the air because some of these deals will go on hold for six months and for any of the systems, that’s fine. They’ll tell you, “We’re really excited. We’re definitely going to move forward. Let’s plan to have a follow up in six months.” And I’m left there thinking six months is half, it’s a lifetime for us. I think you need to have, if you’re going to enter big deals with big corporations, hospitals, health plans, you need to have the cushion to you know be able to plan. You need to have the funds to plan for what could be a 12 to 18 months sale cycle and followed by also an intensive implementation timeframe. The good news is that once these systems are on board, they’re also very – it gets very sticky so it’s hard to bring them on board but once you have them they stay with you. So turn is much slower than you would see in other industries. In fact, we see negative turn for our business.

Alejandro:        Got it. Got it. Well, that’s pretty cool. So I guess right now moving into the actual financing aspects of the business, so how did you – how have you really valued the business? And like when you were going out and you were in the middle of the financing rounds, so how was the business valued in those different rounds? How have things changed from the last round that you did to let’s say you know for example the seed round that you did, you know, back in the day? I believe in total you guys have raised 20 million, is that right?

Carlos Reines:             Yeah, that’s correct. We’ve done just under 20 million over three rounds of funding. Very different ways to value the company depending on the round. When we—you’ve alluded before the first time we met was right about the time we were doing our seed round. At that time, we had an idea. We had our first version of our product and we were just starting to go to market so as many people do the first round, we did it in a convertible note, just easiest way. You don’t have to spend all that time to try to negotiate or figure out the value of the business when you don’t have any reliable metrics to rely on. So we did a convertible note with pretty standard valuation cap, 20% discount and that was our seed round. We did about 1.3 million. And then a couple of years later, we did our Series A forming another round. At that time, we had penetrated a few markets. We were you know already making revenue sale. That’s when we started being valued on the revenue but also the fundamentals of the business, how many providers are being engaged with the solution, how much value are they able to drive for their organizations to make sure that we have a sustainable model, what’s the margin in any of these implementations that we do the cross margin and what’s the growth versus any trend that we have. And I think that’s where you need to adapt it to the type of business that you are in.

Alejandro:        Right.

Carlos Reines:             I think I have a lot of friends, founders that are in a more of a traditional tech and for them it’s just growth and they’re happy to operate with the clarity of 40% annual turn. I think our pace of growth is slower because it’s healthcare but at the same time having negative turn is something that adds to the value. These were the main considerations also for our Series B that we raised more recently alongside some of the big partnership that we’ve done. So for the last year, a year and a half, we had developed relationship with really large organizations where we’re just getting in and that holds a lot of potentials and that was also something that Series B investors took in to account when valuing the business.

Alejandro:        Got it. I mean in terms of like for example the due diligence process, did you experience the process being a little bit heavier as you were maturing a bit more in the financing cycle or it was always you know as [0:12:52] say, you know, regardless of the stage.

Carlos Reines:             Definitely the Series A was much more intensive to seed round. I think the seed round happened a lot more organically where we started with a few angels which barely do any diligence. They just want to get to know you and do they trust you. First, the angels they are not investing in the business. They’re investing in the founders. So there was almost no business diligence at the beginning. Then we had a couple of funds who again, [seed stage funds 13:24]. They’re also investing mostly on the person but they also see the people who have invested before as a very good endorsement to the business. So I would say seed round a lot less diligence than the Series A. The Series A was the first time where we went through serious business diligence, legal diligence. We had to do a lot of clean up, things that we had never done to structure before and that for the B we already had gone through that once so we had infrastructure more in place but as you say, Alejandro, Series B was even more detailed business diligence with [0:14:03] funds. And one of the things that was interesting is we saw under Series A how lead investor did the diligence and a lot of the co-investors take it back in that diligence while under Series B all investors wanted to do their own diligence. So they were sharing some of their analyses but everybody wanted to take their own look, get references from customers and partners, get to know the team. So we sort of had to go through multiple diligence as part of the Series B because we’re getting several groups to lead the investment.

Alejandro:        Got it. Got it. And man, those financing rounds, I mean they kind of like take an emotional toll and it’s a roller coaster of emotions. I mean I guess for example in your guys’ case, how did you deal with it? I mean what was the process of really dealing with that level of stress?

Carlos Reines:             Yeah. It’s always incredibly stressful because you are not fundraising as a full time job. At this time of year, doing the fundraise you’re still doing sales. You’re still doing implementations. You’re still recruiting. You’re still managing operations. So it’s not like anything stops and then you have to add fundraising on top of it which always involved a lot of travelling, meeting investors in both coasts. For me personally, I work out a lot. I found that through the last two rounds the time that we’re doing fundraise I’ve been more committed to early work outs, running, swimming and just working out of the gym. That’s how I got my energy and how I got to disconnect. This last one was particularly intense for me because of all the weeks that the year has, our Series B closed the same week that I was getting married.

Alejandro:        Yeah. I can’t imagine the stress. Oh my god.

Carlos Reines:             Yeah. On top of raising a round, I was also planning a wedding and dealing with a lot of family members travelling internationally and all that, so it got very, very intense.

Alejandro:        Yeah. Got it. Got it. And for example, in these last rounds, in that process, were you guys just like heavy focused on just closing it with the investors that ended up coming on board or was it a competitive process where you had other term seeds and it was more about deciding you know which one was the right partner?

Carlos Reines:             I think it was a little bit of both. So we started the process in the fall and we started talking to a lot of the investors. A lot of them we already had relationships. For health IT, it’s typically a very specific type of fundraise. What we found is for a business like ours which is rather complex and  it’s dealing with providers and payors, investors outside of healthcare are not as comfortable so it’s a much more limited set of funds that they’re going to look in to if you like ours. And we had a lot of interactions. We obviously had you know some rooms that we really had us favourites and all the groups that we were also interested in talking to them. I think we were driving towards the groups that we wanted and we put a lot more focus on them. So there were many groups who will express interest in investing but they were either not the right fit or we weren’t aligned on the structure of the deal. Some of those you know non-market or non-standard terms. We wanted to have a clear term sheet so we didn’t spend a lot of time with the groups that had said that they would want to have more structure in their deals.

Alejandro:        Yeah.

Carlos Reines:             Eventually, we found what I would describe us a rock star line up of investors. If you ask anyone who closed the round, they’ll probably say that because you know who’s not going to say nice things about their current investors. But we were able to close the round with that was co-led by HLM Ventures which is unquestionably one of the leading health IT funds based in Boston. They’re healthcare super experts. They’ve done many great deals and they’ve been incredibly helpful. And then we also had Optum Ventures which is ultimately it’s the technology arm of United Healthcare and they have a venture fund, great partners and currently strategic so unquestionable value. And we also brought along Centene Corporation which is a big group, a conglomerate of health plans to incredibly align with what we’re doing.

Alejandro:        Yeah.

Carlos Reines:             When we started the fundraise, I guess that would have been the dream set of investors and it was a very long process. It took a lot longer than we thought. We almost run out of money which seems to be a trend for all our fundraise where we push it really hard with the runway but it was a really good outcome.

Alejandro:        That’s great. That’s great. And for example with these investors that ended up coming on board, what was really the process of finding them?

Carlos Reines:             So the first group that we signed the first term sheet, we had met one of their partners a few years ago when we were doing Blueprint Health, health IT incubator in New York and more recently we had reconnected with them through another investor. That was the first group. They accelerated us through the process. They looked at the business and very quickly they invited us to present at their partners meeting. Funny story, because they were based in Boston, I was taking a super early train from New York, and when I was on the train there was a big storm and the tree fell on the tracks.

Alejandro:        Oh my god.

Carlos Reines:             So the train stopped in New Haven and said we’re going to turn around and go back to New York and I was like well, this is a fund that we’re really interested in bringing on board. I can’t miss this meeting. I started to look at Glides and ended up finding a zip car by the station. Got on the zip car, drove like crazy to make it to the meeting. Got there like you know 20 to 25 minutes late. The cofounder had started the meeting but we were able to make it, meet the partners, meet the team, do our presentation and ended up with a great relationship. So it worked out really well and then through them, once we had signed a term sheet with them, we started to work in partnership to bring along other investors and they were very helpful making the introductions. I think we still had to do all the work. These guys want to do their own diligence. We had to meet partners in both coasts so it was still a long process but sitting down with them and strategizing around, right, we have all these other folks that are interested where we want to focus our energies to try to close a round the next couple of months and that was that. That was in partnership with them.

Alejandro:        Got it. I mean I think that that was definitely a good way to pass the famous thing that people call us the layer of social proof, no, because there’s a lot of founders out there that think that aligning more meetings may result on you know maybe like cold emailing or going on LinkedIn and stuff like that, just messaging people left and right is going to get them more meeting. But you know definitely it’s more meetings but doesn’t mean more money. So you know I think that was definitely a really, really great way to get that social proof in motion.

Carlos Reines:             Yeah. I think one of the mistakes that we made in this fundraiser actually in between the Series A and the Series B is that we thought about fundraise as a one off thing, right? You need to raise money then you go to the market. You raise and you go back 100% of the business. You actually have to keep doing it. You have to be doing it all the time. You have to keep relationships. You want them to get to know your business and you want to keep them up to speed so that when you are actually looking to raise funds, you don’t have to spend all the time educating people, building relationship because they’re always going to be doing it against the clock. So I think when we did our Series A we’re very happy and then we stopped talking to investors pretty much until two years later when we were starting the process for the Series B. And I wish we had had some more continuity. Even if you are not actively fundraising, just keep in touch, keep them up to speed, keep them in relationships because eventually they’ll become very, very helpful.

Alejandro:        You know, that’s such a great point. I’m a big fan of for example like the investor newsletters and not just for the existing ones but then for example for other potential ones that you think might makes sense to bring on board where you’re maybe sharing like milestones for KPIs, how those are progressing over the time and maybe you know sharing them on a quarterly basis so that you’re keeping people in the loop. I’ve seen a lot of people do that.

Carlos Reines:             Yeah. I think that’s a really good practice. We started doing it after we learned lesson the hard way. And then on top of that, we also you know for the people that we respect, that we have a lot of respect for in the industry and we know that we get a lot of value, we meet with them regularly now. Even if they are not our investors, there are some funds that they have such an amount of experience that just by checking in with them every three or six months, we get a lot of value and that’s also a nice way to keep them in engaged and up to date with what’s happening on the business.

Alejandro:        Got it. So I guess without really going in to much detail because I don’t think this is public, but how aligned were you on valuation for example with your cofounder and maybe with other investors and what was really driving the minimum check that you guys were shooting for in the round?

Carlos Reines:             I think we were pretty aligned on valuation. I mean there’s always a range where you state this is where I’d like it to be. This would be even better. I know this is a little less but I’d be happy with it. One thing that’s important is that both Gil and I looked at the deal as the total package so there are many groups that focus on the valuation but then you know they were taking bad terms. For us, it was actually more important to have a clean term sheet than just focusing on pushing up the valuation. This is something that became the thing in our Series A where we had a really good term sheet for a lot of money but they had a structure that we didn’t like. There was something with the participating preferred. They had some dividends. They had some warrants types zero revenue milestones. A lot of complexity that made it looked more of a private equity deal than a VC deal. I actually remember calling you, Alejandro, around that time to discuss and you saying like that doesn’t make sense at all as a term sheet.

Alejandro:        Right.

Carlos Reines:             And we ended up going with the terms that was a lot cleaner, you know, straight, plain vanilla terms and that is something that makes your life easier in the future because when you’re doing a Series A, it’s 4 million, you know it’s easy to think it’s not that bad. It’s not the end of the world if I had $4 million of participating preferred. It’s not that much. But once you’ve done that, the Series B investors are going to want at least the same terms. So we ended up raising almost $14 million that we would have now almost $18 million of participating preferred and that’s become a lot more meaningful. So we’ve always optimized for let’s get clean terms, valuation has to be accurate because we don’t want to get completely diluted but having a valuation that’s just inflated is not helpful either because at some point you’re going to face the challenge how do I turn a return for my investors? How do I make sure that when I hire employees they’re getting equity that will be valuable as opposed to just you know hyped up stock options? So I think we’re very realistic around you know let’s find a valuation that work for all parties and make sure the total structure with the other terms and the partner fits our values and goals as a company.

Alejandro:        Yeah. You know it’s interesting that you mentioned this because I always share with founders that you should be not be thinking about the present when you’re raising money. It’s all about thinking about the next round. Even though it sounds crazy but when you are raising and you are in negotiations, you should always think about the subsequent round of financing because whatever you do today is going to impact tomorrow. So I think that it’s much better to like you said to raise on clean terms because if you’re just trying to apply a band aid because you know your runway and you may have to shut down your business because you don’t have enough cash and you just take the first thing that comes in the door, that’s like really applying a band aid to something that may require surgery later on. People need to be very careful when structuring this. So I’m glad that you were able to navigate you know those terms that you had in the past as well like doing Series A in that you were able to get something clean, so that’s awesome. So I guess in terms of timeline for let’s say, let’s talk about like this last round for example, how long did it take from the minute you said, “Oay, it’s time to get out there and raise some money,” until the moment that you actually close the round and you were having a tequila shot with your cofounder?

Carlos Reines:             It felt like it took forever. It took actually a long time. I think we started at the beginning of the fall and the round was closed at the end of March. So it’s probably about six or seven months overall. And then started slow, started having conversations with different investors just you know kick the tires at the beginning of the fall and then the process accelerated a little bit. We signed the first term sheet at the end of December and then things went on hold for a bit. It was a Christmas break. People were on vacation, that connected with the JP Morgan Healthcare Conference where all health IT investors are in San Francisco and spend the week there. So it sort of put things on hold for about three weeks overall and then we resumed, completed the diligence and we were at the point we had the opportunity to just bring all the parties on board and we could have drove in to a much faster closing but there were great investors that we’re interested and they want to do their own diligence and this was the big, this was the shocker for me, right. I thought we just finished diligence with this awesome group of investors. These guys will just take their notes and join the round but that’s when they realized they actually want to do their own diligence so it was like doing like a fundraising inside the fundraise. So through February, we were engaging these couple of groups that we really wanted to bring on board. It took them time to do their diligence and by the end of March is when got everything signed. Well, on process, we thought we started beginning of the fall and by the end of the year we’ll have the money in the bank. It ended up taking three more months and we hadn’t really planned for that so we’re kind of getting a little bit short with the runway but it worked out in the end, not with a lot of stress but I’m glad it worked out in the end.

Alejandro:        Got it. Well, that’s amazing. So I guess one thing that comes to mind now is you have, you’re based here in New York City but you also have operations in Spain. So when you have the structure where you have like two offices in two completely different countries, did that provide or add any concerns towards that investors that you were speaking with?

Carlos Reines:             Not a whole lot. They definitely wanted to look in to it and understand why we had people overseas. Once they looked in to it, they got very comfortable with it. I think that’s partially a reflection of the fact that yes, we have employees in the US and in Spain, but all of our commercial activity is exclusively in the US so we don’t have a commercial operation in Spain. It’s just part of the team, part of the technology team that we have remote because of the abundance of talent in Spain. So I think that simplified it from the investors’ standpoint that we didn’t have two revenue generating businesses in different places in the world.

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Alejandro:        Yeah. Got it. I mean I remembered like in my case I had the same structure. We had the office here as well in New York and then we had an office in Barcelona. And you know we really appreciated that because the engineering talent for example in Spain, I mean we saw it was off the charts and what we really liked was the people were very loyal. And you are not dealing with like a revolving door like what you for example encountering places like New York City where engineers are jumping like from place to place.

Carlos Reines:             Yeah. We’ve had very similar experience. Our engineers in Spain are next level incredibly talented, incredibly committed. I think it’s hard to find the people that are really good and also very good at making themselves part of a culture most of the time but we’ve had an awesome experience. In fact, we keep growing the team there and every time they come to the office in New York, everybody is incredibly excited. They have full agenda day and night every time they’re here and I can see how they are incredibly valued and everybody is really impressed with them, with their talent.

Alejandro:        That’s fantastic. And in terms of like going back to the round then and for the process, was it the two of you heavily involved in it or did you guys divide and conquer? Because I mean we were talking about the fact that when you’re fundraising, investors are still expecting you to execute and to increase the KPIs of the business. So did you guys divide or conquer or did you both go at it at the same time?

Carlos Reines:             Yeah. First of all, you’re 100% right and particularly when the deal is long, when you know as I said we signed the first term sheet in the end of the December and we closed around at the end of March. So it’s not only that the investors are looking at you, they’re also looking at the evolution of the business and you have to keep growing. You have to keep hitting the numbers that you told them you would be doing so you definitely can’t stop executing while you’re doing the deal. At the same time, they want to meet both of us so I think my cofounder, Gil, was a little bit more active than I was particularly with the earlier stage conversations but once we got into deep diligence, investors really wanted to look under the hood. They wanted to meet both of us. They spent a lot of time with us so we had to travel many times to Boston or many times to the Bay area. And once they’re interested in investing, they also want to meet the team. So it took a lot of collective time which I think is probably the right thing to do from their end and for us. It was a really fine balance between you know what amount of effort I’m devoting to the fundraise versus just pure execution. And the same thing goes for customer references that every investor would want to talk to your customers but every prospective customer that’s really large also wants to talk to your customers. So it’s sort of a scarce resource that you can’t over parting them with too many reference calls. So I guess it’s sort of always the same, a lot of competing priorities and it’s sort of an art to understand how to prioritize where to spend more of your energy.

Alejandro:        Got it. Got it. So I guess if you could now like I mean now you have been able to obtain like this incredible experience from going through this multiple rounds of financing so I guess now looking back, if you could give advice to your younger self, you know that you are about to embark on raising let’s say like your first round of financing, what kind of advice would you give to yourself?

Carlos Reines:             So definitely many, many learnings. A few things, I would say focus always on clean terms. It’s something that we eventually go to that conclusion but we spent a lot of time with deals that would have never been a good fit. Definitely give yourself more runway. This has been a trend over the last two rounds where we cut it way too short and you don’t want to be negotiating with an investor when you have been a weeks of cash in the bank because at the point you the urgency, you have the pressure. They don’t have any urgency to get the deal done quickly and you’re stuck between a rock and a hard place. So make sure you start early enough. You budget enough time for this to take longer than you think it will so that you don’t have to be on that tough spot for the negotiation. And then be aggressive and tell big vision. I think that’s one of the things that yes, we’ve been able to raise a lot of money for the business but I think we could have been even stronger at the fundraise. We always depict very realistic view of the business which is positive but the fact that everybody is pitching and you know hyper inflated version of their business, by default any investor that’s listening to a pitch is going to discount anything you’d tell them. So I think we’ve been penalized a little bit by the fact that we explained the business exactly the way it is. Investors discount the value of it because that’s the fundraise thing standard inflation and when they actually look under the hood, they’re very impressed with what we are achieving but that makes the process longer for us. So I think those three things: look for clean terms; give yourself enough runway to be able to negotiate without pressure; and spend a lot of time crafting your story and the vision because you have to get investors excited about your business.

Alejandro:        I love that. I love that. I mean I think really fundraising at the end of the day is all about storytelling. And you know when it comes to raising money, unfortunately time is the worst enemy of the founder, right, because you’re running out of cash while time is the best friend of the investor because they get more time to see how you’re executing on the promises that you gave them when you first met.

Carlos Reines:             Exactly. Exactly.

Alejandro:        Yeah. Well, Carlos, this has been fantastic. So what is the best way for folks that are listening to reach out to you if they want to say hi?

Carlos Reines:             Yeah, absolutely. Anyone can email me. I’m [email protected]. C-A-R-L-O-S at R-U-B-I-C-O-N-M-D dot com. Feel free to reach out with any questions. We can be helpful. We’d love to help other founders that are going through the same journey and hopefully can leverage a lot of the learnings that we’ve gathered from all the mistakes that we made in the process.

Alejandro:        Amazing. Well, Carlos, it was such a pleasure. Thank you so much for being with us here.

Carlos Reines:             Thanks so much, Alejandro.

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Neil Patel

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