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Behind the Curtain of Venture Capital with Mohamed Ahmed

Behind the Curtain of Venture Capital with Mohamed Ahmed

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Publication :

May 26, 2025

Duration :

43 Minutes

Host:

Shawn Flynn

Episode Overview

Episode Summary: The Entrepreneur’s Journey and VC Insights

This episode of The Silicon Valley Podcast features Mohamed Ahmed, an engineer turned founder, investor, and author, discussing the multifaceted journey of entrepreneurship, venture capital, and personal growth. Mohamed shares his unique path from working at tech giants like Microsoft and Amazon to launching and successfully exiting his own startup. His experiences highlight the critical importance of founder mindset and strategic relationship-building in the VC landscape.

The conversation delves into the concept of a founder’s mindset, emphasizing resiliency (the ability to bounce back from setbacks) and robustness (the capacity to withstand pressure without breaking). Mohamed explains how awareness and self-reflection, using techniques like the “Five Whys,” are crucial for maintaining mental equilibrium amidst entrepreneurial challenges. He stresses that building such a mindset is an ongoing habit, not a one-time achievement.

Regarding venture capital, Mohamed debunks common misconceptions, emphasizing that VCs primarily invest in people and that relationships built over time are paramount, far more so than a single pitch. He advises entrepreneurs to regularly provide VCs with “snapshots” of their progress to build trust and demonstrate their capabilities. The discussion also covers the importance of seeking “smart money” – investors who offer strategic support and network connections beyond just capital, drawing from his own experience with 500 Startups.

Finally, Mohamed provides invaluable insights into preparing for and navigating the sale of a company. He underscores the necessity of separating one’s personal identity from the startup’s identity early on. Post-exit, he strongly recommends a period of decompression—a “year off”—to recover, reflect, and learn from past experiences before embarking on new ventures, illustrating this with a powerful paragliding analogy about waiting for the right conditions.

Key Points Discussed:

  • Mohamed Ahmed’s Background: Engineer to founder, investor, and author, with experience at Microsoft and Amazon, and a successful startup exit.
  • Entrepreneurial Mindset: The importance of conditioning oneself in physical, mental, and emotional dimensions, likened to climbing a mountain.
  • Resiliency & Robustness: Core components of a strong mindset, enabling founders to withstand pressure and recover from setbacks.
  • Self-Awareness: Using methods like the “Five Whys” to understand emotions and thoughts, fostering a responsive rather than reactive approach.
  • VC Relationship Building: VCs invest in people; trust is built over time through consistent updates and interaction, not just pitches.
  • “Smart Money”: Prioritizing investors who offer strategic support, networks, and guidance over just large capital infusions.
  • Vetting VCs: Assessing compatibility based on how VCs engage with your vision and values, not just numbers.
  • Company Sale & Transition: The need to separate personal identity from the company.
  • Post-Exit Recovery: The critical importance of a decompression period (e.g., a year) to reflect, learn, and recondition before starting new ventures.

Mohamed Ahmed

Resources Mentioned

Transcript

Narrator: You’re listening to the Silicon Valley podcast. On this week’s episode, we sit down with Mohamed Ahmed, an engineer turned founder, investor, and author, to explore the real mechanics of venture capital, startup life, and personal growth. Mohamed brings his unique perspective from launching a successful startup, exiting, and now advising others through the VC lens. Whether you’re an entrepreneur, investor, or someone navigating your own career transition, this episode is filled with real talk, valuable frameworks, and unfiltered stories you won’t want to miss.

Shawn Flynn: Let’s start this week’s episode of the Silicon Valley podcast. Enjoy. Welcome to the Silicon Valley podcast with your host, Sean Flynn, who interviews famous entrepreneurs, venture capitalists, and leaders in tech. Learn their secrets and see tomorrow’s world today. Mohamed, I’m super excited for this week’s episode of the Silicon Valley podcast. I’ve researched your background. We’ve had a prep call before. We were just talking for a good amount of time, catching up on our times in Vegas and all those things that we can’t share with our audience. But for our audience, can you give a little background of your career, some of the things you worked on? Let’s give them a little history before we dive into the questions.

Mohamed Ahmed: Absolutely. First of all, thank you very much, Shawn, for inviting me and being here with you. It’s a pleasure. I’m an engineer by most of my experience and by education. I studied computer science and even did my PhD, going really deep into technology. I did the natural progression from graduating from UConn, the University of Connecticut, and I went to work at Microsoft and then Amazon. I enjoyed those experiences a lot.

But I had a story around entrepreneurship. When I was doing my PhD, one day, they decided to move us from one classroom to another because there was some maintenance they had to do. In the School of Business, in one of the available classrooms, I was entering the room and found a small piece of paper on one of the desks. I picked it up, and it was talking about an internship to work at what was called the Innovation Accelerator. It was a joint program between the University of Connecticut and the State of Connecticut. They would bring in graduate students and entrepreneurs to help them in their go-to-market strategies. I applied, and my main motivation was just to make some money. It was my first year, and I wanted to buy a car. That’s all.

I loved the experience. I worked with the entrepreneurs; it really inspired us. At the end of the program, I was talking to the person responsible for the program, and I told him, “Look, if next year, if I don’t go and work for Microsoft or Google…” And he looked at me and said, “Why do you need to go and work with those companies?” I was just thinking, “You know what? Why not?” Since then, he touched a point deep inside: “Why not?” This was something I was saying I might do one day, but with that question, he made me purposefully work towards it. I took a couple of courses, and I loved the whole space.

After that, I worked at Microsoft and Amazon, but having this in the back of my mind, I really wanted to do this. I wanted to make a startup. So around eight or nine years ago, I built a technology startup. I went through lots of experiences, the highs and lows of a typical business. I made many mistakes, and we’ll probably talk about these in a bit. But midway, I realized I was making all those mistakes probably because there was something wrong with my perspective, the way I looked at the overall experience. With the help of mentors and people around me, friends and family, I was able to turn the ship around. Eventually, we were able to sell the company.

And I said, “You know what? Entrepreneurs do not need to go through this.” Since then, I’ve been on a mission to really help other entrepreneurs work towards having the right mindset and perspective. Since I sold my company, I’ve been working with entrepreneurs to help them have the right mindset, the right perspective, and work towards building their company while building themselves. So this is what I do.

Shawn Flynn: Can you go a little bit deeper on that? Are you talking more about mental wellness or the grit that you hear people talk about, that mental grit? Or what is the mental building component? And then I’m really curious to dive into your understanding because I know you’re an expert in VC and that industry and how it really works. But before that, tell us a little bit about this mental component that you work with founders and entrepreneurs.

Mohamed Ahmed: Absolutely. First of all, let’s take a step back and think of the journey of entrepreneurship differently. The way I think about it is pretty much like climbing a mountain. When you climb a mountain, if you talk to any mountaineer, no matter how experienced they are, they would have to condition themselves prior to starting their journey. That conditioning happens in multiple dimensions: physical, mental, emotional. They make sure that everything that might impact their journey is well-conditioned and prepared so they can start the journey and predict that journey until they reach the summit. Entrepreneurship is the same thing.

Mindset, by the way, is just one dimension. Even though I mentioned mindset, I think there are multiple dimensions that you need to prepare for. So, we’re going to zoom into mindset. If you think about your entrepreneurial journey, you need to make sure that you can withstand failures. We’re going to talk about resiliency and robustness in a bit and how that impacts your mindset. You want to make sure that you’re financially ready for that. You want to make sure that you have the right network. You want to make sure that you’re even physically ready for that. You want to make sure that your own personal brand is ready and will grow with your company. So there are so many dimensions you need to work on.

Now, when we talk about mindset, I would describe it as having two elements that impact your mindset: resiliency and robustness. I’m an engineer, so I will always refer to things from an engineering perspective. If you’re an engineer and you’re building, let’s say, a bridge, and you want to say this is a resilient bridge or a robust bridge. Robustness, when it comes to engineering, means that if you apply some sort of pressure on a structure, it should be able to withstand that pressure and not break. Cars driving on the bridge, the elements – you want to make sure that this bridge is always maintaining its function and its shape. This is robustness in engineering.

Now, if I reflect this to your mindset, it’s the same thing. Let’s say you start your journey with a lot of optimism. You believe that you can do it. When you start facing challenges in your journey, does that change your mindset in a way that would be permanently something different—a negative mindset, for example—or can you withstand that pressure and still maintain the proper mindset? So this is robustness.

When it comes to resiliency, and again, if we map this or get the definition of resiliency from engineering, resiliency means that if the pressure is strong enough to cause any kind of deformation of that structure, when you remove or alleviate that pressure, the structure will go back to its original form. Think of it like a rubber ball. When you apply pressure to it, it changes its shape. But let’s assume you remove that pressure; it goes back to its shape.

Let’s map that again to the mindset. If, let’s say, you really go through an event that takes you out, can you go back to the proper mindset or not? Or would that event leave, as we call it, permanent scars on you, and you’ll not be able to go back to your original mindset? This is really important if you have the right perspective about your mind. What does it mean to have a resilient mindset? What does it mean to have a robust mindset? That would allow you to always think about your mind as something that you always need to maintain, and you always need to build it within your mindset in a way that would allow you to keep going. You’re not drifting into a negative mindset. You’re not drifting into a scarcity mindset and making this a permanent trait. You want to make sure that you’re always adjusting, always coming back to the original form.

So that’s when it comes to the mindset. How do you maintain it? You have to have the resilient mindset, meaning it can go back or should go back to the proper form. And also, you have to have some robustness, which means that you’re not allowing everyday events to take you out of balance. This is key to many entrepreneurs because you’re going to face a lot of those unexpected events almost every day.

Shawn Flynn: So how do you train for that? Is it maybe the “shiny object syndrome” where you get distracted, or someone says something and you break down? How do you condition your mind for those two areas to persevere?

Mohamed Ahmed: That’s a great question. And I wouldn’t say there’s one fixed strategy to do all of that. But the first thing is to be aware. Awareness of your mindset and awareness of yourself is number one. That usually comes by just asking the right questions. I adopted the Five Whys from engineering. This is something Toyota invented back in the eighties: asking the Five Whys so that you reach the root cause of any problem you’re having. Amazon adopted that, and I’ve seen it firsthand or experienced it firsthand at Amazon in different places.

I believe you can apply the same thing to how you feel. Sometimes I take a walk, and I do a check-in with myself. “How do I feel right now?” “I feel stressed a bit.” “Okay. Why?” Then I get the first answer, “Because this happened in the morning.” And then the question is, “Why are you feeling stressed about it?” “I think I’m going to miss the deadline.” “Do you really think this is going to make you miss the deadline?” “Okay, maybe yes.” “Okay, what if you miss the deadline? Does it mean that you’re going to lose your job or you’re going to lose the whole project?” Keep asking those questions. With that, you get to the level of, “Okay, maybe you shouldn’t feel that stressed. Maybe it’s not that big of a deal, or maybe it is, but there’s an action you can take. There’s something you can do immediately and fix that.” So the first thing is just being aware. And one tactic to do that is asking the Five Whys.

The other is also developing what we call emotional intelligence or emotional awareness: being aware of what is going on with your emotions and your thoughts. This is, again, one thing a lot of entrepreneurs fall into that trap. When we usually get hit by an external event, the first thing that happens is an emotion is triggered inside us. Those emotions could be fight or flight, or it could be anger. It could be any of those common emotions. The problem here is that those emotions start feeding your brain, then you start generating thoughts accordingly, and those go with the emotions. If your emotions are really negative, you’re going to start generating negative thoughts: “I’m going to fail,” “Things are not going to work.” Then those thoughts actually feed into the negative emotions, and you just go into that downward spiral. That loop is something you need to be aware of and break.

So you don’t become just a resilient person by doing certain tactics, and you’re done, or you don’t build robustness once and for all. It’s a habit you build, and it’s a lifestyle. Every time you face something, like the examples we mentioned, you start asking questions: “Why am I feeling this way?” or “What can be done about that?” “Can I ask myself the Five Whys so that I reach a conclusion that allows me to respond, not to react?” Those are the things that will allow you, at the end of the day, to become a more resilient person. It’s not something where you get into this classroom, you build resiliency, and you’re good to go for the rest of your life. That’s not going to happen.

Shawn Flynn: Alright. Now, pivoting the conversation. The question comes up quite a bit with the “why, why,” probably more than five whys, of “Why hasn’t this investor invested in me?” or “How do I get in connection with these VCs?” How can you break down the VC industry for us and how it really works behind the scenes?

Mohamed Ahmed: That’s a great question. When you always hear the common statement that VCs are investing in you, that’s true. But if you try to understand what that means, it’s going to make you way more successful. So when VCs say they’re investing in you, they have to know you. And that means relationship really matters.

I remember in my early days, I got advice from an entrepreneur. He said, “Just go to that area, have as many meetings as you can, make sure you have your pitch ready, all your numbers lined up, and you can get the funding.” I did it three or four times, and I failed. I realized at the end of the day, VCs are just humans like us. Even though they’re geared toward investing money and having good ROI, they value relationships. They invest based on the trust you build with them, and that takes time.

Now, the question is, how do you do that? Is it just by inviting them to coffee or dinner? Is this how you build trust? This is part of it because you definitely need that face-to-face interaction. They need to know you, your preferences, and so on. And also, the same thing for you as an entrepreneur. VC is a long-term relationship. You need to know them. But in reality, what you need to do is to allow them to take an accurate snapshot of you and your business from time to time. This is what I usually tell the entrepreneurs I work with.

When I go and meet a VC, let’s say I still have an idea, and I’m still trying to find the VCs that would be a good fit for my startup. You need to go and tell them how you think of your idea, what progress you’ve made so far, and share all of that. You’re not expecting them to tell you, “Yeah, okay, take my money.” They’re not going to do that. That’s just one snapshot.

A few weeks, a few months later, depending on how fast you can make any kind of progress on your idea, you need to go and meet them again. And then, “Since last time we met, this is where my company was, and I did these steps. I built the MVP. I acquired the first two or three customers. Now I’m building the next version of my product,” and so on. Maybe it’s time for you to ask for money, maybe not, but you need to give them yet another accurate snapshot of what is going on with you. This is how you build trust.

Over time, they went from one snapshot to another. They would see and assess how fast you can move. Do you have a common business sense or not? Do you have realistic expectations? Are you pushing your team and pushing yourself or not? Are you on the right track? Of course, this is given that your idea is viable and good. This is something given. Building relationships with VCs in a meaningful way needs to happen over time. You cannot just do it over two weeks.

I know that the media sometimes contributes to the misconception about VCs as well as about entrepreneurs. Most of the time, we see an article in TechCrunch or other blogs or news outlets giving you a picture of two or three entrepreneurs. They look happy, sitting on a couch, and they tell you, “Look, with those six slides, they were able to get $20,000,000 in funding.” That’s it. They don’t tell you what happened in the background. They don’t tell you the relationship that was built over time and how much they had to invest with the VCs of their time and effort. Also, the VCs had to invest with them, wanting to trust them or build that trust and invest in them eventually. Everyone just sees the tip of the iceberg. Then, unfortunately, first-time entrepreneurs think that this is all they need: a good pitch deck and a good meeting, and they should be able to land the $10,000,000 they need. That’s completely wrong. That’s one of the biggest misconceptions you’ll find in the industry.

Shawn Flynn: A buddy of mine, he’s known a bunch of investors going on fifteen, twenty years now, I would say. And he just came up with a new idea, and his million-dollar seed round or pre-seed will probably get done in a few weeks. On the surface, it looks like he was able to do this in no time at all. But when you ask him, “How long do you know this investor?” “Oh, fifteen years.” “How about this one?” “Oh, twenty.” “How about this one?” “Oh, I did these deals with him in the past,” and this and that. And then you start realizing the relationships, and it’s not overnight. Not at all.

Mohamed Ahmed: No, not at all. I would say I never had an investor that invested in my company that knew me for less than a year. Anyone that invested in my company knew me at least for two or three years, if not more. Some of them even ten or fifteen years. And then when I came up with the idea, and even despite all of that, they had to vet the idea. They had to even sit with me within the context of the startup multiple times and ask me multiple questions. They grilled me about my model and about my product. This is the reality. This is how you make business. And as Simon Sinek said, if you don’t know people, you don’t know business.

Shawn Flynn: So with that, how should a founder or a company that’s not based in Silicon Valley, that wants access to the investors here, how should they go about planning, building those relationships? Should they have a salesperson that’s full-time here? Should the CEO be here full-time and the team someplace else, or back and forth every other month? What would be a game plan to build those relationships?

Mohamed Ahmed: You have to be in the area. There is no alternative to that, and you cannot outsource this to a salesperson or anyone else. If you’re the CEO or the founder, you need to be there. That’s why all the accelerators, like YC and 500 Startups, all the others, they usually ask entrepreneurs to be in the Bay Area, at the very least during their fundraising period and while they’re building their company. Maybe they can relocate after that, because in later stages, it’s all about the numbers more than the entrepreneur. But if you want to build relationships, if you want to get the initial investments for your company, you have to be in the Bay Area.

There’s no one size that fits all. You do not have to be there full-time for an extended period, but at least you need to meet them in person. You need to be there, shaking hands. The old way of connecting with people is something you cannot beat. That’s the only way for you to really build a deep relationship.

I would also say this: it’s a two-way street. It’s not about them trusting you and then just giving you the money. It’s also the other way around. You need as an entrepreneur to vet the VC. You want to make sure that their style matches your style. You want to make sure that you’re also acquiring smart money. In other words, they’re not just giving you the money and forgetting about it. You want to make sure that they’re also supporting you with their network, with their know-how, with their experiences. So how do you do that? You can definitely do some virtual meetings, but interacting with them in person and sharing some basic day-to-day experiences makes a huge difference.

Shawn Flynn: What other ways could you go about, or maybe dive a little deeper, into vetting the investors? What are some tricks or strategies or ways that entrepreneurs can make sure or have a higher conviction that these investors they’re talking to are the right ones for them?

Mohamed Ahmed: It comes from how they react or respond to your pitch deck or to your business idea, first of all. I’ll share an example, a story. I was one of the judges for one of those startup competitions. One of the entrepreneurs started by sharing their personal idea. And I loved it very much because it felt so personal. I felt that they believed in the idea because it was based on their own personal experience. And then they won the competition.

I started talking to different VCs. I told one VC back then, “Look, I know that you guys sometimes just need the hard numbers, and you want to hear how big the market is, what exactly they’re going to do, and so on. How did you feel about the story part?” And he told me, “I loved it.” “But what about the other guys?” He said, “Yes. There’s a different style of VCs who just want to get into the numbers, and they don’t like the stories.” And I asked him that follow-up question, “Do you think that entrepreneurs can also partner with those VCs?” He said no, “Because that is a sign of incompatibility. They did not value what the entrepreneur values.” So this is number one: how the VC interacts with your communication style and what you value the most in your business is a big deal. That will tell you if those guys are investing based on your own conviction of the idea, or they just need to see the hard numbers and they don’t care about anything else. So that’s number one.

Number two, of course, is talking to other entrepreneurs that they funded. It’s the same thing. You validate what the VCs value by proxy using those entrepreneurs’ stories. “Why do you think that VC invested in you?” “How did they help you after they gave you the money?” And so on.

So the number one thing, in my point of view, is to see if the VC, especially in the early stages, would truly connect with you and your idea and your motivation behind building the startup. If they’re not able to connect with you, they’re probably going to give you the money, and they’re not going to support you. Whether that’s part of their model or not, that’s a different story, but the result is the same: you’re just going to get the money, and you’re not going to get enough support for you to be successful.

I have a personal story myself. I initially raised millions of dollars. I did not actually see this in my startup. So I raised my first three million dollars, and the VCs were completely passive with me. They were not really digging deep. Then one day, I decided to join 500 Startups, the accelerator in the Bay Area. They gave us only $150,000. But you know what? It was the best $150,000 that I raised out of all the pre-seed or seed rounds. For a very simple reason: they gave us $150,000 and they said, “Come and join one of our cohorts. We’re going to teach you about marketing and about sales. We’re going to teach you how to validate your idea much quicker than what you’re initially doing. We’re even going to try to understand what you value and what you like and what you do not like,” and so on. You know what? That $150,000 saved my business more than the 3% I got initially. It made a huge difference for us. Why? Not because of the money. It’s a fraction of what I raised earlier. But because of the tremendous support they gave us in almost everything.

That’s what I always recommend entrepreneurs: raise smart money as early as possible because you’re going to learn a lot. Don’t get distracted by big check sizes because that, you know, could actually lead to your eventual failure. You can get the money, have a lot of resources. You think that you need to spend more. You keep spending and moving fast, but you know what? You’re moving fast in the wrong direction because you have a lot of money. As I learned at AWS, scarcity drives innovation; it’s not abundance. You need abundance, and you definitely need to have the money. But when you’re 100% sure about your success and growth, if you’re still initially validating the idea, more money does not necessarily mean you’re going to be successful.

Shawn Flynn: What happens in a situation where a VC says, “Oh, I’m smart money. I’m going to provide all these resources, these connections, open up my Rolodex. I’m just a phone call, text away.” After they write a check, they’re pretty much MIA. They have this other portfolio company that’s really taken off that they’re putting all their efforts in. But what happens to companies there, and how do you fix the situation when someone comes in with all these promises and then doesn’t fulfill any of them other than just the capital part?

Mohamed Ahmed: I would actually try to address this beforehand. One thing I usually advise entrepreneurs to do is when they talk to VCs, send them a regular, monthly newsletter, and add a section at the end of your asks: “What are you asking for? How can they help you?” Ask them for intros, ask them for feedback, anything you need to make you successful in the next stage. And just note who is actually willing to help you and support you, who’s giving you that intro. And those are the ones you really need to work closely with. So, to avoid that situation, you can use that tactic or strategy.

Now, if you’re already in that situation, it’s tough because once you’ve taken the money, and that’s why it’s a big deal to take someone’s money—it’s not just you take it and forget about it. Sometimes it’s good to have those hard conversations with them. Pretty much like when the board would have those hard conversations with the CEO, it’s the same thing when it comes to talking to the VCs. I would tell some of the entrepreneurs, “You know what? You need to go and coach your VCs because they probably have the resources, but sometimes they lose track of how they can help you. And you need to bring them into your boardroom and tell them, ‘Look, these are my biggest blockers, and you guys are going to lose your investments if you do not help me with these.'” So, there’s also a role that the entrepreneur needs to play there. It’s not about them promising you and you expecting them to proactively bring customers to you or bring interest to you. You have to go and tell them, “Look, I have that person in this specific company. I know that you’re connected with them through LinkedIn, and can you make me an intro? All I need from you is this email.” Make it as easy as possible for them. That’s also another misconception that takes place with first-time entrepreneurs sometimes. They think that VCs are going to proactively go and make the intros. It happens, and this is definitely what the top-notch VCs would do. If you want to make sure you’re accounting for the average VC interaction with you, you need to be clear and explicit about what exactly you want from the VC. That, I guess, would help a lot.

Shawn Flynn: Okay. So we’ve talked about misconceptions with venture capital. We’ve talked about mental strength. Let’s combine a little bit of everything we’ve talked about into Mohamed, you’ve sold a company in the past. I think more than one, actually, or at least one. How did you mentally prepare for that sale, and what were the… let’s start with that. How should a founder prepare themselves for selling a company that they’ve built, that they’ve put their life into for many years, and then the sale and the transition?

Mohamed Ahmed: Not easy. As far as gaining the right mindset, it’s actually in my book, which I just released three months ago. It’s called The Inside Out Entrepreneur. There’s a whole chapter dedicated to separating the identity of the company or your startup from your own personal identity. And that happens early on. A lot of entrepreneurs confuse their own identity with their startup. The startup is them, and they are the startup. And I understand why that confusion happens, because at the beginning, they’re the sole decision-makers. And, of course, their early customers do business with their company only because of them. They trust the founder. They trust the CEO, and they do business with the company because of the CEO. The problem is that over time, entrepreneurs confuse their own identity with their company. Now, it’s important from time to time to have that checkpoint and say, “You are a company. You are actually much bigger than the company.” So it starts at that point. That’s why I recommend entrepreneurs to just have those heartfelt check-ins with their mentors and their advisors, asking that question: “What if they are not the CEOs of their companies right now? What exactly are they going to do next?” And just have that in mind. It starts at that point. So that’s number one.

Now number two, when the company gets sold, that’s definitely one of the hardest moments, I would say. Even though you may feel happy that you’re not the only one running the company, the pressure of running the business will be significantly reduced. But you know what? You’re going to start seeing yourself losing control over everything. The team that used to report to you, they now report to others. You do not have as much control on the budget and the product decisions that you used to have before. That actually requires a very special transition that requires a mentor. The first thing you need to do, and I got lucky when I sold my company, my mentor actually helped me through that because he went through the same experience. He told me, he basically showed me around the corner: “You’re going to feel this. You’re going to feel that. And you’re going to feel the temptation of building another startup.” And that truly happened. Two or three months after selling my company, I went back and talked with my mentor, and I told him, “You know what? I think it’s time for me to go and build another company. I sold this one. I’m done. I’m going to go and build another one.” And he told me, “Whoa. You need to hold your horses. Just wait.” “But I can’t wait. I have all that experience, and why not? I don’t want to just go and work back again as an employee.” And he told me, “You know what? Just trust me for that, and just wait for a year. Go and invest in your family relationships. Go and invest in yourself, and just wait for a year and see what you think.”

And I actually did that. And he told me, “You know what? You’re like someone who was in a big fight. When others are looking at that person, they will say, ‘Your face just has a lot of blood on it.’ You’re not seeing it. You’re telling everyone, ‘I’m good. Everything is great. I’m going to go and build another company.’ But everyone looking at you, they see that you’re exhausted, and you have lots of wounds. You have a lot to fix.” And he was right. One year after selling the company, when I started to decompress, I felt that, “Oh, okay. There’s a lot that I needed to fix.” And that’s what I usually recommend entrepreneurs: just wait for a year.

Shawn Flynn: What were some of those lessons that you learned both personal and business in that year off, or maybe even longer than that year, between when you sold it to the next thing that you worked on?

Mohamed Ahmed: A lot. Actually, I learned more in that year than what I learned in the previous four or five years. I’ll tell you why. That year gave me a chance to replay everything over and over again. Without the everyday grind of building a startup, that didn’t exist. So I had to replay everything and think again and again, “Why didn’t my fundraising initially work?” “Why didn’t this overcome that?” “Why did I lose that key employee or one of my co-founders midway?” Replaying all of that actually bottled up lots and lots of learned lessons that I wouldn’t be able to get otherwise. So that’s number one. Waiting for one year is a great productivity time. It was a super productive time, even though I was not intentionally doing it when everything was just replaying in my mind. So that’s the key learned lesson.

Two, if you’re building another startup, if you plan to go and build another startup, you want to make sure that you’re not building it with the same old mindset and the same information and knowledge that you had from the first startup. Because what worked in the first startup is not necessarily going to work. I’ve seen that. I’ve seen a lot of entrepreneurs because they feel that their identity is to be that co-founder and that CEO. So they would say, “I want to go and just keep that identity.” They want to have that continuation of their identity, so they go and build another startup. But you know what? Their next startup is just version 2.0 of the first one, not a completely different project, not a completely bigger market. As a result of that, I’ve seen entrepreneurs not make it the second time, even though they feel that they made it the first time, but they don’t make it the second time because they’re exhausted. They’re not able to. Again, if we use the same analogy of mountain climbing: imagine you went to Mount Everest, you did the greatest achievement ever climbing a mountain, and you’re just coming down. And then, towards the end of the trip, you saw one of your friends, and they said, “You know what? Let’s go and do another one immediately after.” Would you be able to make it a second time? I don’t think so. Because you’re exhausted, you need to decompress. You need to learn. You need to recondition yourself. So that’s a key learned lesson for me. I was not doing it intentionally at the beginning. I got lucky again enough that I had a mentor that did it more than once, and he went through that experience and he told me, “Just wait.” And waiting is really important.

I’ll share this from a real-life experience. I did paragliding at a certain point. And paragliding is a really fun sport, but it could definitely be very dangerous because what you do is you stand on a runway, at the end of it is a cliff. You need to wait for all the good conditions, and once the conditions are ready or in your favor, you run as fast as you can so that before the end of the runway, your parachute will take you off. Now if you rush it, you’re going to crash because the conditions are not going to be in your favor. You’re not going to have enough wind; it’s not in the right direction, and you’re going to crash. My coach in paragliding was urging me to do that. But I made one mistake one day. I kept waiting for forty minutes, and I got bored. I said, “You know what? I really want to do it.” And I kept running, and I reached the end of the runway, and I almost took off. But because the wind was not really stable, it pushed me back towards the mountain, and I broke my leg as a result of that. It was a big accident. The doctor told me it’s “one out of ten,” ten being the worst, “you’re number nine.” You had a really bad one. It took me a year to recover.

The same thing applies to entrepreneurship. Waiting is sometimes in your favor. You learn, you adjust yourself, you wait for the right conditions, you wait for the right idea. You make sure that you’re ready for that jump, and then you go for speed. If you rush it, you’re going to crash. Or maybe not, but you’re just leaving it to chance. Don’t do that because the cost of building a startup is huge.

Shawn Flynn: And, Mohamed, with that, can you mention your book’s takeaway or that you’d like people to take away from your book in this interview? And then also, what’s the best way for anyone to learn more about yourself, where they can get the book, and follow your work?

Mohamed Ahmed: As I mentioned at the beginning, the book is based on what I learned throughout that experience and all those stories that I shared. And there are different things. Again, the main idea behind it is before you get started with your entrepreneur journey, whether this is your first time, second time, or third time, you need to have the proper conditioning. The entrepreneur is the most important building block of any startup. Yet, it’s the most vulnerable piece of that whole experience or the whole ecosystem. So if the entrepreneur is not ready, then the startup is not going to work. And the book is all about that.

We built a community around it called Boundless Founder, and the website is https://boundlessfounder.co. If you go there, you can find the link to the book. It also exists on Amazon and Goodreads. Anyone can go ahead and definitely buy it. I would love to hear the feedback from your listeners. By the way, it’s available on Kindle Unlimited, so if you have Kindle Unlimited, you can read it for free.

At the end of the day, I really want to make sure that any entrepreneur is just going through problems that are an upgrade of the problems that I went through. I don’t want them to feel that they’re still making one mistake after the other, not because they didn’t know the solution, but because their mindset was not in the right place. So the book is all about that. And we also have the community around it, as I mentioned, Boundless Founder. Anyone can register for free. They’re going to get our weekly newsletter. We also have some free training courses and guides just to help founders get started with their journey. And again, keep that resiliency and robustness as you move along the journey.

Shawn Flynn: Fantastic. And with that, Mohamed, I want to thank you for taking time to be on this week’s episode of the Silicon Valley podcast. And for our listeners out there, I’m not the host of the Silicon Valley podcast. I’m an investment banker focused on mergers, acquisitions, growth capital, secondaries. Connect with me on LinkedIn if you have a business or would like to talk about one of these transactions. I’d also thank our partner, Finales, who’s been a big champion of the show. Check them out as well. For our audience, if you want to check out our past episodes, don’t forget to go to thesiliconvalleypodcast.com. And Mohamed, once again, thank you for all the wisdom and stories that you shared on this week’s episode of the Silicon Valley podcast. Thank you very much, Mohamed. And we’d like to add a little disclaimer. The views expressed are my own and do not necessarily reflect the views of Finales Inc. or Finales Securities LLC, member FINRA SIPC. Thank you for listening to the Silicon Valley podcast. To access our resources, visit us at thesiliconvalleypodcast.com and follow our host on Twitter, Facebook, and LinkedIn at Sean Flynn SV. This show is for entertainment purposes only. Before making any decisions, consult a professional.

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