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From Employee To Entrepreneur With Alex Malebranche [Episode 52]

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What does long term thinking mean to you?

We all have our own ideas of what this means – and this changed based on where you are in your life and business journeys. In this week’s episode, Doug C. Brown talks with Alex Malebranche, the founder and CEO of PlaneAhead, a company that finds the best flight offers and exchanges your tickets if your flight prices drop. Alex and Doug discuss long-term thinking across various stages of business, moving from an employee to an ownership state of mind, profitability, and much more.


In this episode you will learn:


Episode’s guest – Alex Malebranche

CSS 52 | Employee To Entrepreneur

Before getting his degree in Accounting, Alex Malebranche was an Intelligence Analyst in the U.S. Army. He has been able to use those unique skills, in conjunction with his traditional education, to work in a varied amount of industries. Alex started his career at Amazon and AWS and went on to build the Delivery organization for Plume, a smart Wi-Fi company that is now valued at over $2 billion USD, as the first employee hired in the organization. Now, he is a passionate and dedicated husband and father in addition to being the Founder of PlaneAhead.

Visit his website: planeahead.co


From Employee To Entrepreneur With Alex Malebranche

I am bringing you another great guest. His name is Mr. Alex Malebranche. He owns a company called PlaneAhead. It’s a cool concept about how you can take travel on domestic airlines in the United States and have protection on the cost of your ticket. How it works is you book something, let’s say it’s 60 days earlier and the price drops over time, then you’ll get a credit back on that if you are a part of that PlaneAhead network. We’re talking a lot about profitability. We’re also talking about how do you move from employee-state-of-mind to the entrepreneurial-state-of-mind?

A lot of times with entrepreneurs, even if they’re existing and doing well, they forget about what it’s supposed to be about in the beginning. They get their business in a rut. They’re stuck and not sure what to do. They’re working in the business and then not stepping out of it to look back at what was the beginning supposed to be like. Maybe it was that at the beginning and what it came to be. I’ve talked with several people who have very successful companies but they’re not happy in the business itself because the business has them. They don’t have the business. We’re going to talk about those factors. Get your pen, pencil, your digital notepad out, and let’s go to the interview with Alex now.

Alex, welcome to the show. Thanks for being here.

It’s a pleasure to be on. I appreciate you having me.

I wanted to focus on a couple of things. I certainly want to talk about profitability, especially how it relates to sales because I know you were a sales rep on Plume and AWS, is that correct?

At Plume, I did a little bit something different but at AWS, I was in territory and enterprise sales.

When my AWS account all went crazy then I had to spend hours with AWS fixing it, you’re the guy who set it up, right?

Partly. I will take full responsibility for it but I did help get you set up.

You then made the break to entrepreneurship from that point. I’d love to talk about what is that transition point because we have people here that have billion-dollar companies who listen. We have a lot of entrepreneurs as well that would be going from point A to point B or they’re at point B trying to get to point C. They’re making mistakes that when they were starting their company out, they had to pay attention to but now they don’t have to so much.

They still should and that’s what gets them in trouble. Inevitably, when they call me, they’re like, “I’m doing X, Y, Z.” I’m like, “What happened to the letter before X?” They go, “I forgot about that.” That’s where it gets them stuck. I want to talk about it in the context of what it takes that transition because, for a lot of people, their entrepreneurship has taken off. I like to tie in the whole profitability side. From salesperson which corporate sales executive and an entrepreneurial role in itself, what got you finally to make the break from point A to point B?

Reassess what you want your life to be like, and then adjust your business around it. It's not so much the money we make in terms of revenue. It's having a lifestyle and building profitability around that lifestyle. Click To Tweet

It was serendipitous, I’d say. I always wanted to be an entrepreneur in my lifetime but it was more important for me to be a family man. Many entrepreneurs out there, sometimes those things work against each other. When you’re an inventor or an idea all the time, you take time, money, and effort away from what you would hope to be a family. I had always said to myself, “I want to be an entrepreneur but I want to make sure that if being an entrepreneur is in my future, it comes to me. I want it to be very natural. I don’t want to chase after things.” This idea came when I was on paternity leave.

I was trying to make a change myself but realized that I couldn’t. I looked for a company that did something similar and figured out, “There’s a gap here.” For me, the transition began because of that promise I made to myself, “Now that time has come, it was my opportunity to lead into what I believe to be a passion of mine.” For a lot of entrepreneurs, when you’re talking about entrepreneurs, they have done it 2, 3, 4, or 5 times. At some point, they’re running on autopilot like they love it, know it and so they do it. You spoke to skipping steps along the way. When you do it the 2nd or 3rd time, you might skip some steps because you feel like you’ve done it before.

Sometimes that works for some people but for the majority of people, it’s always about the root of why you became an entrepreneur to start, which is you’re passionate about this thing. With that passion comes, you’re researching, trying to understand that more, talking to customers, and you are a customer. That is important when you’re trying to decide to make the transition rights. Are you going to be as committed this time as you were the very first time?

I’m a sports guy. I liken it to when you hear the to-better-off-this-first contemplating retirement. They find themselves thinking about retirement the moment they get into training camp and they think to themselves, “I’m not into this as much as I was before.” That’s what I think about it as. For me, it’s giving yourself that gut check. Are you as passionate about what you’re doing? It is not the outcomes or potential money but the subject matter. Are you passionate about it this time as you were the first time? That’s going to help you a lot with making sure that you’re taking the right steps at the very beginning.

I think that’s critical in any business. I remember Steve Jobs saying when he was alive, “If I have too many days that I’m asking myself, do I like this anymore? It’s time to make a change.” What you are saying is extremely important for people to remember because a lot of times people will get into business. They will even have success in business but then the business is like, “That’s not what I wanted it to be.” It starts to wane the passion in that process.

That translates directly into the ability to sell. Even if the company is growing, they’re losing money because they’re not in the game. It’s going through the motions. What I heard you say was you started with your values first and those values were family first. You’re like, “I’m going to have a life like this then I’m going to build my business around that so my business supports my life versus my life supporting my business.” Did I get that correct?

That’s well said.

That is so important. That’s part of the reason people lose the passion for what they’re doing in business because the business now has them. They don’t have a business. I was talking to a gentleman. He cut his company back, eventually. He was doing $200 million. He cut his company back to $50 million and he said, “He’s never been happier than he’s ever been.”

CSS 52 | Employee To Entrepreneur
Employee To Entrepreneur: Entrepreneurship is very taxing, convoluted, and complex. You can get so wrapped up in a lot of other things. Focus on the thing that made you start in the first place.


Again, the thing that made you start in the first place. You can get so wrapped up in a lot of other things. Entrepreneurship is very taxing and sometimes convoluted and complex. You start to take on a lot of other responsibilities and people’s money. You can very easily lose the Genesis to why you started. That story does not surprise me.

A lot of times with entrepreneurs, I agree with that if they’re getting out there. People are reading now going, “That’s me,” I would challenge them based on what you said. Go back and reassess. What do you want your life to be like and adjust your business around it? It’s not so much the money we make in terms of revenue. It’s how do you have a lifestyle? What profitability do you have around that lifestyle? That was one of the things you and I originally first spoke about. Not on this show but in our previous conversation about, how do you make sales profitable? How do you live a decent life in doing that?

Let me pull you back to AWS for a second then go back to your company because I love the concept of what you pulled together. When I saw it and I was like, “Oh my God.” By the way, folks, there’s a waiting list now. If you sign up for the waiting list, we’re going to tell you how to do it. Even myself, I want on the list. I want to get into this thing. We’ll tell people what that is in a moment but let’s go back to AWS like the days you were selling enterprise accounts.

A lot of people are trying to figure out, how do I sell an enterprise account? How do I make it profitably from the sales standpoint? Smaller companies or mid-sized companies are spending a lot of money getting into these enterprise accounts. Sometimes, when they look at it, they go, “It took me two years to get this thing and my profitability is less if I had done ten medium-size accounts in the same timeframe.” How did you guys do it at AWS? Did you have a profit model or do you? How did it go?

It’s very interesting. I think AWS or Amazon is very unique in this way like in many other ways, which is probably what makes them Amazon. In the sales motion, the idea of selling is a little bit different than maybe a classic eight years account executive role. We were looking for opportunities within an account that wants to do business with us already. This is how my career started. When you think of sales, you think of cold calling like, “I’ve got this thing. Do you want to use it? We think this brings this A, B and C value.” A lot of times, with AWS in particular, people call us and say, “We want AWS.”

That part of the sales motion is done. The sales motion for us is more like, “Now that you’re using us, we are growing and have these many different services, it’s on us to know enough about your business to be proactive in saying, ‘Of these 150 services that AWS has with your specific industry and business, these services are going to be the most impactful for you.’” It’s a different classic sales motion but it’s very much in the mindset of being an entrepreneur.

You’ve got to know the business, understand and proactively identify where there’s an opportunity for us to help them do better in their business. By selling them “another service” or more services that are going to help them do better in business, their business grows, and therefore, they spend on us as opposed to, “You pay us $30,000,” then that is our profit. It’s more of a long-term mode of thinking because ideally, we’re trying to save the company money. “With this service, you’re going to pay a little bit but over time, it’s going to save you money and effort. That’s the value.” When I first got into AWS, one of my KPIs or things to focus on is how can we help the customer save money, which would in turn keep a long-term relationship and make them happy.

A little bit inverse of the typical sales strategy but I think it’s applicable in a lot of ways. As we move forward in business, it’s as much about how will we bring value and maybe cutting costs and giving the customers an opportunity to buy into the idea of cutting costs. It is a little bit different but it was a unique experience for me.

The world is a beautiful thing. Start traveling. Click To Tweet

As far as selling into the enterprise, anybody that has sold into an enterprise knows, that one of the major things to consider is the hierarchy or the organizational structure. It is office politics. Who do you have inside of the company that is your champion? Who are the people that require a little bit more work as far as what you’re selling? Being able to navigate those personalities and how those things work again, is applicable to a lot of different things as well.

Alex, what’s the name of your company? I’ll let you announce it.

The company is called PlaneAhead. I’m super excited that I was able to identify something that I felt like people would need again, to that idea of finding a solution that helps people save money. We’re selling the idea of membership and you pay us money but ultimately, I hope to save you more money than you end up paying PlaneAhead, which is the idea.

I know you as a long-term thinker in our conversations. If we take Amazon and we replicate this, as you said, it’s a little inverse of what we normally do in sales but it’s Amazon. They’re not a tiny little company so they have been thinking long-term. I’ve never spoken with Jeff Bezos but I imagine if I had talked with them or had the opportunity to talk with them, I know in the beginning they were losing money consistently and they kept bringing investment money because he was always thinking long-term or it appeared to be. When we’re in a sales process and we’re thinking long-term, in your case, you were thinking cross-sells throughout the whole process, what do we sell more?

Maybe we’re saving some money for the client or our margins are even a little less than they were on the first initial sale but we’re picking up a multitude of services on the backend. It goes back to McDonald’s. Like them or hate them, they’re a successful company. They started the bundling with the Happy Meal. Amazon is bundling the process together over time and therefore, gaining long-term client value, which I can only imagine, increases this stock share like crazy to take a look at it. I see you doing the same with your company because you built your company. You got to a place where it’s running then you’re like, “Let’s look long-term. Let’s get some investor money into the process and let’s grow this company out.” I love the concept. Would you tell people about what PlaneAhead is all about?

PlaneAhead is a travel tech software where as a member, we’ll track and change your plane tickets after you’ve already purchased them and before you’ve taken the flight. What that means is if you’re planning ahead to fly and go see family in August and you bought the ticket now. Let’s say that ticket was $500. Between now, when you bought it, and eventually when you take off, that price continues to fluctuate. Whether it’s because of international conflict, gas prices, or whatever the case may be, it continues to go up and down. A lot of people try and play the game of like, “Is this the best time to buy? I’m going to keep on waiting for it,” then they make the purchase.

After you make the purchase, people typically don’t go back and check on it but it continues to go up and down. What we do is anytime it goes down after you’ve already made the purchase, on your behalf, we’ll go to the airlines and say, “There’s a credit that needs to be given,” and you’ll be allotted the credit back from the airline. If you bought your ticket on American Airlines one day and it was $500 and then next month it goes down to $400, the same exact flight, American Airlines would give you $100 credit back. We’re not changing morning to night or anything like that. It so happens that the same flight goes down $100.

What a lot of people don’t know is that they will do that for you but, of course, they won’t market to you that they will do that. It’s one of those things where it allows you to take advantage of something that’s already in place on behalf of the airlines. Also, it enables you to continue to travel where at times, some people are getting a little stir crazy at home who were wanting to use their time that is remote working to go see more parts of the country or the world. Now we’re able to do that by giving customers more airline credits for the money that they bought. It’s the new way of guaranteeing the lowest price.

CSS 52 | Employee To Entrepreneur
Employee To Entrepreneur: The sales motion is knowing enough about your business to be proactive in saying, “We have these services that will be the most impactful for you.”


They put it back in a travel bank, basically.

Every airline is slightly different but yes. You don’t get cash back because it’s a non-refundable ticket. What they do is issue you a travel credit. Whether it be Alaska, United Delta will issue a travel credit. The next time you want to go book a trip, you can use that travel credit.

For all you road warriors out there or soon-to-be road warriors, this is an awesome concept. I didn’t fly as much as others, Alex, but sometimes, I would be on 30 to 50 flights a year. I never ever check the price of the ticket after I already purchased it. I would do what you said. I would be like, “I’ve got it down. If I get it to fifteen days ahead or on a certain day, I would notice the airlines were changing the prices here and there then I would try to buy it.”

Sometimes, I wait until the last minute then I get a decent rate but you’re gambling at that point. Basically, what you’ve done is you’ve taken out the gamble of the whole situation where it’s like, “Buy your ticket.” If that drops down before you are there, you’re going to get a bank credit or check back or something like that based on the fact that they’re in your membership club, if you will.

A lot of customers will ask when I explain this, “If it changes more than once, do you keep getting credits?” The answer is yes. We had a customer that gave us their Thanksgiving plans in May in advance and it went down nine separate credits for $16, $8, $38, and $4. It continues and it adds. Again, as I said, when you’re ready to travel the next time, use all those credits and go somewhere else. No need to gamble. It continues to rack up for you.

Does it matter where somebody flies in the world? Can they fly to Europe or Australia?

A lot of the airlines that are US-based had transitioned to rules that allow this to happen. If you’re traveling to Europe on a US carrier, for instance, like on United, yes, you can do that. A lot of the international carriers have not made the transition with their rules to allow for this to happen. If you’re traveling from the US to Dubai on Emirates, it’s less likely that you’ll be able to take advantage of our program yet, because now, everything is continuing to change, especially in the travel space. Now, most major US carriers, no matter where you’re traveling to, if it’s on a US carrier, you’ll be able to take advantage.

I’m curious. I’m pumping you full of information here. Let’s say I start with the US-based carrier that’s an Alliance like Star Alliance or whatever. I remember one time I went from a US carrier then their flight got grounded due to issues. They put me on another Alliance member and they took me to Germany at that point. Is it still covered because I bought a US ticket?

Seeing the world opens people's minds, creates empathy, and creates better human beings and greater experiences. Click To Tweet

Whenever the change is made, it gets a little hairy when airlines make the change for you. When they cancel a flight for whatever reason, call it a lack of resources now and there’s a staff shortage. If you were on United and they transferred to Lufthansa because that’s the only one they’ve got left, it’s no longer eligible for that. As an example, United is in control of that change.

They have given you over to Lufthansa and now you’re not able to get that same benefit but there are a lot of hidden gems within the airline rules. For changes like that, there can be an opportunity for you to reap some benefit or incentive because of that change. I would implore people if they’ve got the time to take a look at how many things are within the airline rules that are in your favor but again, they make them difficult to get through for a reason.

The last question would be what does a membership cost?

A membership cost depends on how many people are on the membership. For a single membership, $99 all the way up to a family membership, which covers four people, $149 and that’s for a year. To give a frame of reference on average now and each credit change is $176. On average, people get their money plus more back in a credit change. That’s an average, so not every ticket gets changed now. We’re seeing about 30% of the tickets that we have purview of to get a change but we’ve gotten someone a credit of up to $816 once before on one trip. There are opportunities there, especially as the world and travel are very volatile. It creates an opportunity for people to take advantage.

The reality is this is a direct savings. Let’s go back to business travel, for example. When we can save money in any capacity and we’re not affecting the overall outcome performance, that’s key guys and gals. If we can reduce our costs but still have the effectiveness and the efficiency that we want, that translates into a direct increase in profitability in any situation within any company.

Travel is one of those things. There are some companies that spend 8 to 9 figures sometimes annually or maybe even more, and some of them on employee travel. If you’re doing employee travel and you can save this money, you can bank it toward the bottom line profitability, which increases the overall profitability. If you’re a publicly-traded company, it helps with your stock price and all kinds of things. Also, lets you do initiatives in a company that maybe you couldn’t do. Maybe you take that money that you’re saving on playing fair and put it into some type of employee fund that you never thought of or whatever.

The money is either going to go to the airlines or it’s going to go back into your credit account of some sort. I have had this conversation so many times with entrepreneurs and people who own businesses. They’ll go, “I got a $17 million company.” I’ll go, “What’s your profitability? How much money do you make? We’re losing $300,000 a year.” If somebody is going to start, you made the switch, you moved, you’re going in the end game, and you’re building your life side out. Do you look at revenue or profitability? Do your investors look at revenue? Do they look at profitability? Which one is the more important or are they both equally important?

It starts unique in that. At a certain scale, neither of those things matter. I think I’m at that scale now. We’re trying to prove the hunger and the viability of something like this. We’re proving out whether this is something that will be a help to businesses and airlines or is it going to be seen as more of a threaded? This is more of a testing phase for us. Thankfully, a lot of the tests that we’ve been doing are all positive. A lot of people, for instance, might think, “The airlines are going to find out and they’re not going to like it.” It helps airlines. It has people booked direct then, if you get $70 on United Airlines, the next time you fly, you’re going to fly United. If you’ll buy a $300 ticket, you save $70, which you’re happy about, but then you spent another $230.

CSS 52 | Employee To Entrepreneur
Employee To Entrepreneur: Focusing on how you can help the customers save money will, in turn, keep a long-term relationship with them and make them happy.


Doing a lot of those things is our focus now. Eventually, we’ll shift over to what the profit is for us. When you’re talking about a tech company, those things can be a little bit more complex to realize. You could be losing money for five years before you start making money. Again, it’s about focusing on what value we’re bringing to our customers and the value that we’re bringing to the travel ecosystem, in my opinion, when it comes to an offering like this.

Airplanes is a small part of it when people start flying. Now, we’re talking about tourism around the world. We’re talking about hotels, rental cars, and all of these industries that in the last few years have been taking a major hit. Now we’re starting to increase the economy of all of those different things. There’s a larger outcome and things that we’re focused on when it comes to this industry or at least that I’m focused on with this industry.

I would say we’re uniquely for a startup now, neither sales nor profitability are my top concerns. There are things that as we grow, as you spoke to those margins are important for us to realize how much effort we’re putting into a company or a customer. We put in less effort but still get the same amount of performance or the same amount of value for our customers, so they continue to use us year over year.

That’s a good way of looking at it. You got long-term thinking going on. Maybe the theme of this particular show should be long-term thinking and growth and how that means still ultimate profitability for companies. Alex, if people want to get on the waiting list, how do they do it?

PlaneAhead.co. When you go on our landing page, you’ll see a bunch of buttons on the top and the bottom, all around that say, “Join our waitlist.” It doesn’t cost any money to join the waitlist. Put down some of your information and as we start to open up more spots with some are of the scale that we’re able to open up, we’ll get you in there. We’re trying to serve as many people as much as possible. My goal is to see people around the world. It’s not to do anything but that. The world is a beautiful thing.

I started traveling when I was younger. I joined the Army and got to see a lot of the world. Seeing the world open, people’s minds create empathy. It creates better people human beings and greater experiences. That’s my overall goal. You’ll also start to see more about our waitlist because it’s fairly new on our Instagram, on our LinkedIn, or anywhere you can find us.

Alex, thanks for being here. I agree with you. Nothing will broaden your horizons like traveling to other parts of the world and understanding how people are people there too, especially us as Americans. That’s not a dig at America, folks, so don’t send me hate mail. Alex is a veteran of the United States Army. I am too. We love the country but nothing will broaden your horizons like going out, being in other cultures, and understand how they deal with life is very similar to how we deal with life as well. Alex, thanks for being here again. I appreciate you being here on the show.

Doug, a blessing to be here. Thank you for having me.

You’re welcome.

If you want to save some money on your airfare, now you know how to do it. Go to Alex’s company and think about the long-term in your business. We talked about how to think long-term. When you look at Amazon and you look at any big company. It took time for them to get there and they were all constantly thinking down the line, most of them. There are a few exceptions where the business grew without them but most people are thinking long-term.

If you’re starting up as an entrepreneur and you’re reading this or you’re a seasoned entrepreneur and your business is out from underneath, let’s talk about the long-term. What do you want to do long-term? Build your life first and build the business around it. Check it out on the PlaneAhead. Go to the waiting list if you want to be on that. They’re going to be opening it up as soon as they can. Start saving some money because that directly goes to the profitability of your business and your life so you can reallocate those funds to other needed resources. That’s it.

If you desire a specific subject matter on this show, as always, reach out to us. Let us know what it is. We’ll source the talent. We’ll get that subject matter for you. If you like this show, which I’m assuming you do. Please go up and subscribe to it if you haven’t already subscribed and please give it a glowing review if you feel it deserves it. I appreciate you being here.

If you need any help with your business on hiring, managing, recruiting or retaining top talent or how to get your sales team or yourself into the top 1% of your sales in your industry globally, reach out to me at Doug@CeoSalesStrategies.com or @DougBrown123. That’s my LinkedIn or company phone number at (603) 595-0303. Go out there and sell something, sell a lot of it, sell it profitably, and make a lot of money. Have a great day and a great life. Until next time. To your success.


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