About Maha Ibrahim
Maha Ibrahim, a general partner at Canaan Partners, discussed her experience in venture capital and the firm's investment strategies on the podcast *ANGEL* in February 2023. Ibrahim noted that her first day at Canaan was March 23, 2000, and that "about two weeks later we went into a nuclear winter for several more years." She stated that Canaan is a series A investor and that by the time a company goes public, the firm has typically been involved for seven to twelve years. Ibrahim said that after a company goes public, Canaan aims to "get off the board within a year" to distribute or sell stock, adding that "our job is to put money back in the hand of our limited partners; it's not to sit on public stock."
Ibrahim commented on the venture capital environment, stating that "we as a venture class made the bet that a low interest rate environment was going to last for a decade plus as opposed to the door being shut in 2022." She said that "a lot of the financial services investments that have been born out of low interest rate environments are not sustainable businesses in higher interest rate environments." Ibrahim also said that when she has lost money, "it's almost always not because the founder sucked or the tech sucked — it's because I got the timing wrong." She expressed bullishness on security, workforce management, and education technology, stating that "EdTech needs to be disrupted in a big, big way."
Source: AI-verified profile updated from Maha Ibrahim's recent appearances.
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Transcript (69 segments)
H
Host0:12
Since at least the year 2000 and they've made it through the dot-com bust, the Great Recession, and whatever happened in 2022 and will happen over the next couple of years. Today we have an incredible guest: Maha Ibrahim is a General Partner at Canaan Partners, where she has been since 2000. We have an amazing conversation on how venture has changed since 2000, distribution strategies for early-stage investors, valuing startups, the results from LPs being overallocated into Venture, and then her experience as the first investor into The RealReal, the person who helped start All Raise to try to get more women into Venture. We pretty much cover it all. It's a great conversation, it's gonna be a great show, stick with us.
Thanks so much for coming on and talking about—we've been doing this sort of three-cycle investor series, and I'm super excited to talk to you because I'm in all the brands that you invested in, like not as a consumer...
M
Maha Ibrahim2:11
Um, okay. So your GP at Canaan Partners, where you have been since 2000. Tell me a little bit about yourself, your journey, and Canaan and what you do there.
Yeah. It's amazing how time has just flown by. I cannot believe that I have been doing what I've been doing for almost 23 years now. Through, as you mentioned, three cycles, it has been a wild ride. And I think the wonderful thing about this profession—and most VCs will say this—is you just get to meet the smartest, most ambitious people with these great ideas every day. I just feel very fortunate to be doing what I'm doing. A cool job.
H
Host2:53
It is a job. I mean, doing this as I mentioned for a really long time... I started out wanting to be an academic and was on that road. Got a PhD in economics, was pretty much gonna do that, and then I decided that it was a really solitary existence and a pretty isolating profession. So I went to the West Coast—I was on the East Coast at the time—I followed my now husband back to the West Coast and got a job at an upstart telecommunications company called Qwest Communications. I was there for a couple of years, then as a result of that, I made my way into venture. And I spent probably the first five or six years of my venture career really very much a generalist.
M
Maha Ibrahim4:13
Interesting. Rare. I wouldn't suggest that for anyone entering the business now by any stretch of imagination. But it's rare for somebody to look at consumer and enterprise at the same time.
H
Host4:32
Absolutely. And yeah, very different skill sets. How did that evolution come about? Was it just accumulated? Was it because you found The RealReal and you were like, this is it?
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Maha Ibrahim4:39
Totally. Actually, my first three consumer deals: one was Kabam, which was a mobile gaming company that sold for about a billion dollars. The second was The RealReal. And then the third was a company...
H
Host5:10
Tell me about... okay, so let's go to the cycles. So you really started at Canaan in 2000. Was that the entry into venture? Yes. So was it equally bubbly in enterprise software at the time? Was the bubble pretty widespread?
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Maha Ibrahim5:23
Yes. So my first day at Canaan was March 23rd of the year 2000, and about two weeks later, we went into a nuclear winter for several more years. So my first experience in venture was just seeing things... it was a learning experience, I'll put a positive spin on it now.
H
Host6:16
Having come from economics, did you feel like you saw that coming, or was it as much a shock to the system as it was for so many other people? Were you like, 'Oh, what have I done? I've entered this at exactly the wrong time?'
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Maha Ibrahim6:31
Um, I was so early in my career. I was in my mid-20s at the time; I couldn't believe that they were giving me the experience and the opportunity to be investing. So I was thinking about it from that perspective, as well as the perspective of 'Oh my gosh, we're in a macro bust cycle here, and what's going to get us out of that?' And really thinking... it must have been... I wonder if you had an extra awareness.
H
Host7:17
You may have had an extra awareness because I was probably a similar age, came here to the Bay Area in '99 doing sort of consumer technology writing, but I didn't have any broader economic understanding of what might be happening. You're just in your 20s thinking, 'I'm at work, I hope I don't get laid off.' So I do wonder, do you feel like you were sort of like, 'Okay, this is something I can study or something that I have...' You had a broader awareness of the macro.
M
Maha Ibrahim8:11
Where my economics hat kind of mixed with some psychology classes. Economics is very much about psychology. I would sit down with these VCs who had been investing through the cycle and been very successful, and even in 2001, 2002, they were still puffing their chest out, thinking their portfolio was awesome. I'm like, 'Really? Because all I'm seeing are falling knives everywhere.' But then I'd have lunch with one after another, and it was the same. We, as a species, as venture folks, we have to exude... it was just such a facade that was put in place. I can't wait to hear the extent to which you think that—I'm just gonna jump ahead. Do you see that happening now?
H
Host9:19
I will say I certainly have the occasional founder conversation where I think those expectations are still in place, or that facade of 'my business is special,' or 'my investment thesis is so special that this will not affect me.'
M
Maha Ibrahim9:43
So there are several things at play which lead me to think that it's just very different now. One: social media. Everyone is very aware of what's going on. Moreover, there's an acceptance right now that we are in a bad period. People don't know how long it's going to last, but we're in a bad period in terms of fundraising, and that means our companies need to right-size themselves, get more efficient, and reduce their cost structures so they can live to fight another day. It's not like these companies deserve to go out of business; they're not 'bad' businesses. Most of them are good businesses that just got their cost structure way ahead of where they should have been because access to capital was so easy. So I do think it's a very different... they've gotten ahead of their skis from an expense standpoint.
H
Host11:11
Hiring the right person is so hard, and right now so many talented people are looking for work. There was a bunch of layoffs this past year. But where are all these laid-off tech workers? What are they doing right now? Well, they're on LinkedIn, they're polishing up that resume, their landing page, putting their skills on there, getting endorsements. And right now you need to use LinkedIn Jobs to recruit. That's going to be a bar raiser, going to teach the other people on the team how to do even better work in specific verticals and skills. There is no hiring platform that comes close to LinkedIn. It's almost a billion users—875 million users, can you believe it? Better candidates, faster. LinkedIn Jobs helps find you the candidates worth interviewing. Post your job for free at linkedin.com/angel. Terms and conditions apply.
Okay, so back going back in time again. What was VC like? We're just gonna bop all over; we can do whatever. We're under DeLorean and we're taking our trip through where we are in that cycle. What was investing like in 2000, and how has it changed over the years? What was diligence like? How did you do it all without Pitchbook?
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Maha Ibrahim13:21
There were sources of information out there, but certainly not as rich and as prevalent as there are today. The diligence took a long time. It was not uncommon for me to see a company and then issue a term sheet three months later.
H
Host13:47
Wow. We are just coming out of a cycle where it was see a company and issue a term sheet within three days.
M
Maha Ibrahim14:10
Right. Which is why this business has changed so dramatically. A lot of those deals that were getting done were based on Excel spreadsheets: 'Does this business fit into the model of what an LTV to CAC looks like, or sales efficiency, or whatever metric?' If your formula spit out the right magic number, then let's go ahead and do it. That wasn't the case in 2000. It was much more about: 'Do we feel like the market is big enough? Yes. The company is early, but the team looks good and the references are great, so let's dive in.'
H
Host14:50
One of the other things... sorry to talk so much.
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Maha Ibrahim14:52
No, no, please. That's what you're here for.
H
Host15:11
I'd be thrilled. In 2021, if I had a company that exited for $200 million, I'd be like, 'Oh crap.' The high water mark was more like $10 billion or $20 billion, and that's what we were all shooting for. That hasn't gone away, but it's not going to be as common as it was two years ago. Is that a function of check sizes getting bigger so you need returns that are outsized, because funds themselves have swelled? Or is it just that the expectation became more and more multiples?
M
Maha Ibrahim15:52
Molly, this is the chicken and the egg problem you're describing. Which outcome—or my required outcome, whichever you want to call it—was much higher. So it was just this kind of perverse incentive circle or flow. And we all got caught in it.
H
Host16:29
How big is Canaan's fund?
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Maha Ibrahim16:33
Right now, we're investing out of Canaan 12, which is $800 million in size. We are Series A focused for the most part. If I were talking to you in 2015, I would have said all we do are Series As: we want to lead those rounds, take 80 to 100 percent of the rounds, and be... Now we're a bit looser, but Series A and C is still the sweet spot.
H
Host17:21
All right, I'm gonna ask you more about that, but now I have to go back to my timeline. So we're coming out of nuclear winter, it's 2004, 2005. At what point did you go, 'There might be another bubble building here,' or was that bubble really so exogenous because it was over in housing while venture was doing its thing?
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Maha Ibrahim17:36
Oh gosh, not at all. Yeah, we had to convert. This is the fun stuff. The party was gonna happen. It was awesome. You had virtualization, which for obvious reasons did what it did, and then you had mobile and social. And those three combined forces almost concurrently. Almost every company that we now consider big came out of those three trends—maybe not all, but two out of the three. Those three trends were responsible for what we're seeing today. And to put a finer point on it, we're all looking for the next best thing, the next big wave to surf. We've tried the web3 thing, the crypto thing. We've tried... Cast AI audits and optimizes your cloud cost and performance for you, which the cloud companies don't do automatically. They eliminate the stuff you're paying for but don't use, and search for less expensive hosting options within your cloud provider. On average, Cast AI customers save over 60 percent on their cloud spend. Get a free cloud cost audit at cast.ai/twist.
H
Host20:19
And we met with the founders last week, and they are really excited to help founders and listeners to this week's show save on their cloud bills. So give them a call, go visit cast.ai/twist. So I feel like you can look back now and say these three trends—virtualization, mobile, social—and we nailed it. But clearly, much like now, we're all looking for that next wave. In another eight or ten years, we might... like what were we wrong about at that time? Because there's stuff we're clearly wrong about now.
M
Maha Ibrahim21:16
Let's talk about what we've been wrong about. I don't even need to rewind that far. I'll rewind it five years back. Think about—and we've made a good amount of money in fintech, and we continue to be really bullish—but think about the number of financial services investments born out of low interest rate environments that have gone public and been huge. But fundamentally, these businesses are not sustainable in higher interest rate environments. We as a venture class made the assumption... so there's timing bets. What I'm trying to say is, at the end of the day, so much of success in this industry is about riding the wave, but also riding the wave at the right time—making sure you're not too early and not too late. When I've lost money in this job, it's almost always not because the founder sucked or the tech sucked; it's because I got the timing wrong. That's brutal because that is the hardest part.
H
Host22:48
But it also sounds like you're saying the wave doesn't necessarily need to last forever. You just have to get there... kind of a public company. Do you want to be holding that company for four more years post-IPO? Do you want to sell it at this price, or do you want to wait and see if we can ride the wave for two more years and double your money? It's not just about the going in, it's also about the getting out.
M
Maha Ibrahim23:39
Yeah, I like that too because we talk about exits as though the exit itself is so final. But in fact, there's a whole series of events that happen post-exit. If the exit is an IPO, you still have to get it right—you have to know when to distribute, especially if you are... it becomes 2 percent of the IPO as opposed to owning 20 percent of the company that's gone public. Because of the scrutiny and regulatory issues associated with distributing the stock and not wanting to disrupt the float. There's a litany of issues we have to consider, and we'll get it wrong as many times as we'll get it right because timing is something we can't predict.
H
Host24:43
How much are you able or willing to tell us about how you might have handled, for example, you're best known for The RealReal, for being the first investor into...
M
Maha Ibrahim25:10
I'll tell you what we try to do as a policy internally. As a reminder, we are Series A investors. So by the time a company goes public, we've probably been in the company for anywhere between 7 to 12 years. It's a long road. And given that our fund life can be between 10 and 13 years, we want to make sure we actually distribute that stock within a reasonable amount of time. So post a company going public, we want to get off the board within a year because we want those degrees of freedom to be able to distribute or sell the stock when we can... distributing again at any given time. So we try to be very, very sensitive. I didn't answer your question directly about The RealReal, but that's as much as I'll say.
H
Host26:18
But to put a finer point on it, if you own five percent and you distribute, you're saying as an early-stage investor it behooves you to sell as soon as possible after an exit. But the sensitivity you mentioned means you're potentially putting a lot of stock back into the market, which could impact the share price.
M
Maha Ibrahim26:43
Correct. The float and average daily volume is a huge variable in our decision of when and how much stock to distribute at any given time. You know, partners... it's not to sit on public stock. There's a debate right now about when firms should distribute and whether they should get into the business of managing public stock. We are not a fund that is a registered investment advisor, and we don't have a hedge fund attached. We are an early-stage fund, so we don't try to time the market. We don't have enough expertise internally to time the market. There are funds that do, and God bless them.
H
Host28:11
Or maximize all this money. Absolutely. And I also think... we have seen nothing but up and to the right for 13, I would argue probably 15 years. Nothing but up and to the right. When people don't have a history of a negative experience, they just assume it's going to continue until it doesn't. And everyone is rewarded for it continuing until it doesn't. When the music stops, everybody's hurt. So it actually behooves you to continue... the table is a winner—why not? You can see why everybody would want to be sitting at every table.
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Maha Ibrahim29:18
Absolutely, yeah.
H
Host29:21
I mean, given the boards I'm on and the behaviors I've seen, I would absolutely agree. There are people who have been in the industry for 15 years, they're veterans of venture, but they have never seen a downturn. Some of them have never even fired a CEO. Not to say that's a rite of passage, but it's an odd thing. You don't necessarily have to do that when it's been so easy for our companies to raise capital at up rounds.
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Maha Ibrahim30:10
Who was 40? And I thought, 'There should be all this wisdom here, this person is 40.' Then I thought, 'Actually, yes, there is probably a lot of experience and water under that bridge, and yet there's not a downturn.' It might be easier for us to say we've seen this story before and know what's going to happen. There's incredible value in having gone through this trial by fire. What isn't learned when everything's so easy? I'd say there's a bit of envy that I have for people who have only seen up and to the right because it did seem so easy. It did seem... a company that's burning too much money because it didn't matter. I have never lost that. I'm always like, 'Oh my God, this company's burning a lot of money. I don't understand it.' And in board meetings now, those people are learning and will continue to learn. We still haven't seen a cycle of down rounds and recaps. That's coming; we'll see that in the next year or two. People will learn, and then things will go up and to the right again.
H
Host31:49
It does seem like there's value in that too. Not only do we probably think about budgeting and governance differently, and I will get... as a recovery, because you think it's going to last forever. And as a result, you are—or one is—planning for a downside scenario.
M
Maha Ibrahim32:31
Yeah. How would you say over the last 23 years you've seen the average helpfulness of the average VC board member develop? How do you think about governance and what you see happening on boards, potentially by veteran investors who don't have that depression-era mentality?
I think one of the great things about venture growing so much and being so hypercompetitive is that we've all had to be much more helpful to our companies than we ever have been. I don't know one firm out there that doesn't have a services or platform arm helping with recruiting, marketing, go-to-market, legal, or Corp Dev. So if I'm a founder right now, I'm feeling pretty good about leveraging the venture firms I work with in ways that I haven't before. A lot of VCs have stepped up and just gotten off the boards. I've seen that. I've seen other folks spend a lot of time counseling companies on cost efficiencies. I've been pretty impressed by how the venture industry has handled this most recent downturn. Everyone got the message really quickly that belt tightening was needed.
H
Host34:53
How about the outlier startups? Crazy, huh? You can see why deals had to get done in three days, sometimes three hours. It was a feeding frenzy. That's why when I said I'm a generalist, it's so rare. In order to compete in the last 10 years, you've had to be a subject matter expert. You have to find that deal because you were looking in the space and actively pursuing a thesis. If you didn't, there would be 10 other people who would gladly take your place. So it has been, up until six months ago...
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You have been involved in some climate tech investing, I mentioned at the top. That's what I'm doing at Launch... boom. And now we have this kind of crash but also a bit of a bubble in climate. I wonder how you think about these simultaneous occurrences: a bust in one vertical but a baby bubble in another.
M
Maha Ibrahim38:29
I guess this is where the economics comes in. There's a lot of money chasing returns. The returns are not coming from public markets—or if you're day trading and not long, you've been losing money. Maybe returns are coming in mid-single digits from bonds. So where do you find beta? That beta is in venture, in private equity. So what parts of venture right now look awesome? Climate tech is one of them. Early-stage venture is still on the list of what will give me beta, and it will always be on that list irrespective of whether we are catching a wave or not. You do not want to time the market if you are an LP. So I'm raising your question up a little bit to give an answer to that. And is that answer about how bubbles are...?
M
Maha Ibrahim40:15
I dig in a little bit more on this idea of being a thesis investor or having specialties. I wonder as we move into a less competitive universe where we have the chance to be more thoughtful, like you were saying about how diligence used to happen versus now where we talk a lot about accounting spreadsheets and outcomes. Is there an opportunity to be more of a generalist and more thoughtful, looking for outliers? Or is that a rosy nostalgic view of the past?
The latter. It's just too competitive of a business. I have accumulated 23 years of that, and I can always look at a storage software company and then the next day look at an e-commerce startup because I've done all of that before. But in today's universe, if I am looking in one space, I'm heads down on it for a really long time because I have to get smart. Yes, I might have four weeks instead of four days to do it, but hopefully people are taking the time to get to know not only the company but more so the founders: why are they doing it, what's their passion? You see the difference between VCs versus founders.
H
Host42:16
I want to go back to this: early-stage investing will always attract money. Is there a world—just yesterday, the Wall Street Journal published data that venture capital firms raised $20.6 billion in new funds in Q4, down 65 percent year over year, the lowest amount in nine years. Is there a universe where the shine comes off, or do you think that's in the bigger funds?
M
Maha Ibrahim42:48
The shine is not coming off. It might be a little less shiny, but we still have to put money to work. Our limited partners have now an overallocation to private because the public markets have been hit. So to make their own math work, they've had to contract their commitments to privates, including private equity and venture. That will stabilize. But at the same time, the private returns are still good in comparison. And at the same time, private returns will lag. So a company that didn't raise money for two years... readjust itself. Great venture returns start coming in. It all just might exactly so. Because that's the reason we call it cycles. Time is a wheel. And that's why it's always so hard to time things—to time the market and time our exits. That is the biggest variable in success or failure of companies.
H
Host44:37
And do you still feel like—how do you think about timing now, having done this for 23 years, having seen the cycles? Do you think there are patterns that you are in a position to spot that might make you better at timing?
M
Maha Ibrahim45:10
Sometimes, and sometimes no. But then again, those companies went on to raise a lot of money and have nice exits. I'm not sure I've learned anything except to say timing is again the biggest variable. I will say this: with every deal I've done, I try to sit down with my CEOs before the term sheet is signed and say, 'Listen, the chances that this company gets to the finish line—the finish line being a fantastic exit—we don't know what they are. But what I do know is there is a high probability that the company will fail. So let's make a pact: if either one of us thinks it's not working, let's have a dispassionate conversation about what that means, so we don't waste any more time trying to make it work. If you can set those guidelines from the beginning, then timing... you can move on to something that might have better timing. Fail fast.'
H
Host46:39
Fail fast. Or just be aware of what failure looks like as opposed to hitting your head against a brick wall.
M
Maha Ibrahim46:46
I would even go one step further and say be aware that the possibility of failure exists, even though it hasn't existed for 15 years.
H
Host47:11
Sizes around $500 million. There is this tension between 'I'm gonna stick to fundamentals, valuations are bananas but will come back to earth,' and 'You kind of have to play on the field given to you.' It seems like the dance is evolving without losing that core fundamental.
M
Maha Ibrahim47:40
Yes. And so much of it is based on what the core values of the GPs are and how the firm is structured, both from a carry perspective and a... there's a well-established off-ramp. A lot of funds aren't necessarily like that. They govern by monarchy or oligopoly where carry is doled from on high. That's a fine model, but it makes generational transition harder. In those models, it's easier to answer the question of generational transition by just getting bigger and giving people pieces of a bigger pie, rather than keeping the pie the same size.
H
Host48:54
Say more about that. What does that mean?
M
Maha Ibrahim49:13
So in a select few, the management company has value. That value means that if I own half the management company, in order for you to come into the firm, you have to buy out my stake or part of it. That's very expensive because the management company in a growing, bigger firm is bigger and bigger. It can be worth hundreds, if not billions, of dollars in some cases. So buying into that is not easy, and leadership transitions are not easy. There are some structures of firms where the management company doesn't have value, where the... and now I can't incentivize. There will be people listening who are embarrassed on my behalf, but others will be happy I'm asking because they didn't know that either.
H
Host50:13
Molly, I think most people just entering venture in the last couple of years don't know enough to ask that question. When I joined 23 years ago, I didn't know. I just locked into where I am. I have plenty of friends who entered 23 years ago that are no longer in venture because of how their firm was structured. They didn't know. One of the reasons we started All Raise was to educate women about these things. We want to get women to the investing table and keep them there. To retain diverse investors, we have to educate people on what compensation should be, what governance should be, what they should ask for. It's not just about being promoted to partner; it's what is your equity as a result?
M
Maha Ibrahim51:41
You read my mind. My next question was: let's talk about women. You helped start All Raise. When I started at Canaan, there were no other women in the firm. Fast forward to today, 40 percent of the investors at the table are female. We have a diverse set of investors—not just white men and white women. We want to be representative of the entrepreneurial pool. When I started at Canaan, it was by no means an objective of mine. My mindset was... it took me a while to realize that I was cutting off my nose to spite my face. If we want this country to be as successful as it can be, we have to become an industry that welcomes diverse founders, immigrants, everybody to the founding table and backs them—not just with seed checks. That's an asterisk people don't talk about: it's the bigger checks—$20 million, $50 million. Are there enough of those? No, not at all. It feels like one of the things that's happened is that the easiest way to force change is to start firms. But if a lot of women started early-stage firms, and then the founders they invest in hit a wall at growth stage... we've only made so much progress. We'll continue to make progress, but it's a much longer road than I thought.
H
Host54:41
Tell me more about the goals of All Raise for people who aren't familiar.
M
Maha Ibrahim54:46
Aileen Lee brought us all together. There were probably 15 of us at the very beginning. The goal was to get more females at the investing table and make sure they stay there, know what to ask, what to push for, and what equality looks like in a venture firm versus just being happy with the partner title.
H
Host55:31
How are you looking at the next five years? This is a story we are at least somewhat familiar with: we're in a bust, there's going to be an upswing. Give me your best... with the caveat that timing is hard.
M
Maha Ibrahim56:10
I think this is going to be a tough period for at least two to three years. There are still areas that are white hot and will continue to be so. I'm really bullish on security. I'm really bullish on areas of workforce management. We are in a period where the numbers show very low unemployment; I don't believe that at all. People are doing side hustles. We probably have another 9 to 12 months of consumers not dipping into savings as much as expected. Education absolutely needs to be disrupted in a big way. And security.
H
Host57:10
Amazing. I'm sitting here in Oakland where the whole city is being held hostage by a ransomware attack at this exact moment. Lucky you. Maha Ibrahim is a GP at Canaan Partners, where she has invested through three cycles. Thank you so much for joining us on this episode of Angel. This is incredible.
M
Maha Ibrahim57:42
Thank you. It was a pleasure.