Decision Dialogues
Decision Dialogues

Episode 20 · 1 year ago

Bold, Innovative Entrepreneurship

ABOUT THIS EPISODE

On Episode 20 of Decision Dialogues, Jennifer Faherty and Victoria Consoles speak with Deepak Shrivastava, CFO of The Flex Company, co-founder of Porter & Sail, and former CEO of Hotel Credits. Deepak discusses the risks he navigated as he took the leap to start Porter & Sail. He shares insights on how he raised capital and incubated a startup within Porter & Sail, highlighting the value of betting on oneself. 

Get the full show notes and more resources at ModeraWealth.com/DecisionDialogues 

Are you paving the way for the life you want facing decisions that may affect you personally and financially? The decision dialogs podcast, brought to you by Modera Wealth Management, presents personal stories about navigating through life's pivotal moments, narratives that we hope will inspire you as you create your own story. You'll learn what influence their next steps and gain insights that could help you with your own critical choices. Welcome to decision dialogs. Thanks for joining us on decision dialogs. We're thrilled to have you along. My name is Jennifer Farty and I'm the chief client experience officer at Modera Wealth Management Llc. Today, my colleague Victoria Consolis, who's a senior financial planning associate at Modera, and I will be chatting with depack true Bastaba. Depack was a CO founder of Porter and sale, a mobile conciere technology that was recently acquired by luxury escapes, an Australian based online travel company. He also leads hotel credits, on Alternative Hotel booking platform that was incubated at Porter and sale during the pandemic. He currently serves as CFO of the FLEX company, the top selling alternative period chair brand known for creating highly differentiated, sustainable products available in over twenty five thousand retailers in the United States. That is quite a bio, so I'm looking forward to this conversation. Welcome everyone to the show, and Victoria, please take it away. Thanks, Jennifer and DEFAULC welcome. Thanks so much for taking the time to talk with us today. Thank you so much for having me. Of course, this is fascinating. I find that you ran a company through the pandemic, and I'll kind of put a spoiler in there. You ended up selling it through the pandemic as well. So I kind of wanted to to get into that. But first, why don't you tell us where you kind of started out? I know you started in the banking industry and how...

...you got to wanting to start your own business and what it took to get there. Sure, sure, I had my start in investment banking. It wasn't necessarily a mistake, but I will say it was a stroke of luck. I was simply looking for the first job in the best job that I could get that would help me pay my student loans off. Not An unconventional way to think about things in terms of paying off debt. I was lucky enough to land a spot at Morgan Stanley. I thought what would be a two three year stint at most ended up being sort of the first half of my career and that's sort of how I got into banking and then from there basically wanted to explore more of my own stuff, like what my own interests were. After my financial obligations sort of I check the box on them. Ended up taking a spot at dropbox and it's early days, which then, you know, motivated me to sort of start my own business, which led me to the founding of Porter and sill along with my cofounder. That's great. So Porter and sale. What year was that founded in? That was founded in twenty late, two thousand and fourteen. Two Thousand and fourteen. And who is your cofounder there? Was it someone from dropbox or someone else you knew? It was actually a mutual friend, not from college, but through college friends. I had met my cofounder Caitlyn's know, what a wonderful partner. We still maintain a beautiful friendship, even though we've sort of veered off into different, different paths, but we sort of met in July two thousand and fourteen, I believe, and started talking about new businesses. We both were into travel and hospitality. I guess we hadn't stopped talking until we sold the business and we still talk. We actually had a conversation yesterday. That's great. So what type of travel company is it? I know it's featured mostly within hotels. So what were you kind of crafting when you came up with this? And I know you had to raise capital for that, so I want to hear about the process there and what that took. Sure, when we embarked on building the product in the service, but it was really oriented towards was, and this is back in late two thousand and fourteen, early two thousand and fifteen, was sort of a speak to sort of...

...a new mode of traveling. At the time there was a you know, an emerging APP for everything. We knew that there was going to be a growing space and appetite for travelers, for consumers wanting to basically consume travel information. The travel information that was out there, everything from data to where to go, where to eat, when it drank, where to shop, etcetera, etc. was very diluted and not curated. So what we wanted to do was basically provide a very curated, tailored platform for sort of the new age traveler. The medium in which we sort of wanted to deliver that was a little bit nontraditional. We know, we could have gone the route where Victoria I could have convinced you to subscribe for ninety nine cents a year and you have this cool lap. You know, quite frankly, we wanted to take the betob route and what we found out was, look, the travelers that we want to get in front of, the eyeballs that we wanted on our product were essentially living at Boutique luxury lifestyle hotels. So why don't we convince hotel owners and general managers to take on our product, pay for a product and have this be exclusively offered to their guests? So that's where we got started. That's how we started growing our userbase, that's how we started monetizing. From there, we just wanted to invest more and more into the platform, which predicated the need to essentially raise capital and go the the quote unquotes looking valley route to raise multiple rounds, invest into the product and get that flywheel going. That's great. I want to, you know, talk about raising the capital there. So what did that look like for you? Were you talking to investors or people you knew? who were you raising capital from, and how long did that process actually take? It took a long time to raise capital, to be quite can it was a very difficult process. Throughout the life cycle of the company. At different points of the company's maturity, we raised capital from different classes or subsets of folks. Initially we went to friends and family and really attempted to bootstrap the whole enterprise just to...

...get it going. We put obviously our savings, my own personal savings and capital into it, everything that I had sort of amassed in terms of the nest egg I'd built up from my previous years into the business. You have to believe in yourself right your your own best investor, essentially. So it took a little bit of personal gumption to sort of take that initial leap of faith then just put money down to get things going, develop the product, higher team, higher agencies, to essentially get the actual service in business going up and running. Once we started hitting certain milestones and it became a thing where we started devoting essentially full time energy to the enterprise. We then decided to sort of go first seed round and from their goal for a series, a round and intermittently we raised convertible debt, so very different financial instruments. All that being said, you know, we started institutionalizing our approach. So we went to professional angel investors, we went to venture capitalists, we went to corporate VC's as well, so it was a full gamut of folks that have ultimately ended up on our cap table. I have a quick question actually about something you said and also related to the first part of when you're or back in Morgan Stanley. That relates to personal finances actually, because you said at the beginning that you kind of almost did a this is the are my words, like a practical decision to go to Morgan Stanley to pay off your debt and then you ended up eventually pivoting, to use the word Gumption, and then taking your savings out to start this. So can you talk a little bit about like the decisionmaking you had to go through financially from a like practical to kind of taking more risk? Sure, sure, yes, so, definitely it was a very practical route for the first half of my career, right paying off debt, helping my parents with their mortgage, you know, all that family stuff, helping my younger siblings through college, etc. Etc. So took a good almost near decade at Morgan Stanley to sort of accumulate that. Well, so I can check the box and all those things I wanted to accomplish. But then, you know, I came to sort of a personal realization, professionally speaking, thinking through like Hey, am my hundred percent happy here? Is this something that I want to do? Is...

Sort of led me down and exploration into other things. I have an engineering background, although I'm not an engineer, so I was always interested in technology and that's sort of what led me to drop box and then ultimately my own technology and our prize. In terms of personal finances and how I sort of looked at the decisionmaking and how and why I took sort of a leap of faith. I have to say it was quite out reckless. It was less of a pen and paper and alytical decision, which is not necessarily my mo I'm you. Typically my decision making framework at large is very data driven. This specific jump for me was an inflection point that was very intuitive and driven by my gut quite frankly, there was a level of comfort where I had a mask, you know, that nest egg, where I could easily say, all right, I have x number of years of runaway. At the time, I was single, didn't have any obligations, known mortgage, had this nest egg of savings and said, hey, you know, if I don't do this now, I don't think I'll be in a better position mindwise to actually take the sleep of faith. And again, like I have to be my own biggest cheerleader. While I have that gumption, while I have the pension to really want to take this risk and have the ability to take this risk at the age of thirty five, not married, no kid, no responsibilities, I should do it now, because chances are five, six years later, where I am today, with a kid, with this spouse, with obligations, it would be a much harder pill to swallow. The appetite for it definitively would have been less. It's like in the Matrix, like red pill, Blue Pill. Once you're down the rabbit holier down the rabbit hole. I'm sort of on the other side now. You know, I'm glad I did it, but it was financially speaking, if I had sat down with a, you know, a financial planner Victoria, you would have been like, do you really want to give up a certain lifestyle to sort of go take a very, very risky proposition? I'm glad I did ultimately, though, because you know, that was on myself and you know, again, I think in general you can never go wrong better on yourself. I love that and just kind of curious. Did you give yourself a...

...time frame, like, if this doesn't work out in the next five years, I've got to go back to having more stable income or back to not necessarily the investment baking lifestyle? But did you kind of give yourself this all right, I'm betting on myself for x amount of years and then, if not, I'll figure something else out, I should say like quite croozy. I, you know, I had it. And again, this is why my analytical side would classify the decisions as being reckless. I knew that I would have some sort of time frame three, four, five, six years where I didn't need to drastically change my lifestyle, not that I was living an extravagant one, but I knew that I wouldn't have to really change my day to day. I didn't know how long that would be, but I also realized, like my life situation may be different, and it ultimately was. I got married and at kid and became apparent. You know, let's just say that shortens your runaway quite a bit, you know. So I knew that there was a time frame. I didn't put specific parameters on it simply because I think I realize that I know my situation is going to change, my circumstances going to change. So just recognizing that I would need to be agile really really helped out for my peace of mind. No, that makes total sense. And so you took this what you called a reckless kind of chance or with your savings account. So what did it look like then, from managing your personal finances from there on out while also managing the finances of a business? What did that look like for you, because it definitely had to be a huge change. Yes, it was a it was a huge change. There was definitively a wall between personal finances and the businesses finances. A hundred percent. We just knew from the BAT. My cofounder I it's essentially that it's almost like a marriage. You're sharing a bank account literally right with yeah, this is we always kept it separate what was, you know, for me personally and ultimately my family, versus what was in the business. So there was always that divide. Now what bearing it took on my personal finances? Yeah, I would say. What was my approach? If you're asking that, it was sort of, again, I would say,...

...reckless, especially in those first couple of years, and you're just kind of shooting from the hip. For example, there have been multiple instances where we were out doing fundraising. We needed to keep the business going, we needed to make payroll. So guess what, WHO's fitting that bill? It's going to be the founders who are going to run up their credit cards or dip into their savings. At one point I definitely dipped into our or K, which is not advisable for tax reasons. Right. It shows the confidence and that you had in your business and I love that you're able to back up your employees and put them first in those kind of situations. So I feel like that is incredible as well. So can we talk about the pandemic now and what it was like to run a travel company during that? I mean, essentially, everyone was telling you, please don't travel, and here you are running a business that has become so successful and it's almost put out a halt. So I want to hear from you. What did that look like initially and how did that get you to where you are now? As you could imagine, it was, professionally, probably one of the most ficult things that I've ever encountered. You know, it's not even like travel was was down, like you have a business downturn, you expect that, you plan for it. There's contingencies. Right. Travel wasn't like down travel. Travel was illegal, and actually it's something that I one of our staff members sort of equated it to basically being being a drug dealer, because we're here selling a product which is quite literally illegal. So how do you actually go about doing that? It was just a really tough time. It involved multiple tough decisions, both with clients, both with products in our services. We just had two sun set a bunch of stuff because we just didn't have the capacity to sustain him, and also, unfortunately, with staff. Let go about eighty eighty five percent of our staff, shut down multiple offices. It was not an easy time. How big had your business grown to at that point? We had about twenty five full time employees have had the peak. We had a few sales outposts in London, Singapore, headquarters was here in New York and we had some folks in Rome. We also worked with hundreds of contractors as well. Overnight it felt like things just shut down. I...

...remember the day was actually March ninth when things shut down, mainly also march night because it's the notorious big's death anniversary. That's I just remember that day where we literally saw like because we had insight into hotel occupancy rates. It just crashed like single digits, something the industry is never seen before. To answer your question directly, Victoria a horribly difficult time and it's informed a lot about how I approach work and how I approach decisionmaking, especially tough decisionmaking. Today. Personally, I think my previous life or pre pandemic, I probably would very much inclined to either put off tough decisions or try to circumvent them so I wouldn't have to make them. I think it's just best to confront it head on now. We had no choice during the pandemic. There were just too many decisions to make and for the good of the business, we couldn't postpone those decisions. So making those tough decisions like had on, I think, is really important, and then also being swift. I think there I think there's something to be said about analysis paralysis by using the excuse or internalizing the excuse like, Hey, I still need to think about stuff, I need to analyze this, like it's actually just an excuse. You probably already know or intuitively have a gut feeling of what that answer is. You should just pull the trigger, and the quicker you pull the trigger, I think it's better for everyone. I'm a fan of quick and decisive, tough decisions, just going through with it. Not must it be in such a great you know, learning curve really in some respects because you're forced to in this way, but really sometimes it takes so long to learn that lesson. You know, I love what you said about analysis Palysis, because in this situation there's no analysis to do because it was so, so unknown. We had never gone through something like that. You didn't know when it was going to end, so you almost had to make decisions without having information. I'd add that the other thing that emerged from that experience during the pandemic was innovation, right and this is where, like you know, you've heard the cliche like necessity is the mother of invention. It really forced us to think about out our business differently, think about how to work with clients differently, think about how we'd run a business. What emerged from it was sort of this business that we've continued to run, that we incubated at Porter and sale was...

...hotel credits, which, for all intents and purposes, was a completely re envisioned it was like a start up within a start up. It's like we started a new business, but we had to we had to figure out a way to monetize, to pay our bills, to make sure that I could pay rent. Quite honestly, right, it really forced us to just really shift the Dynamic and the paradigm of how we were operating within the industry and it forced us to be innovative in a great way. Do you feel like, after now you've sold the business in things are starting to open up again in the world. Are you still happy with your decision to sell the business there, or was it out of a need personally and financially to do so? I can I can imagine how difficult that must be. Right, your hit with this global pandemic and all of a sudden you made a decision, which I'd like you to talk about, to to sell the business. But it's just a complete one hundred and eighty from, you know, a year and a half ago. So I just like to hear about, you know, maybe any of the challenges or, you know, the successes there with selling the business as well. I don't have any regrets whatsoever. Just like any entrepreneur, you know, you do strive to have it be a big and relevant business. A relevant business doesn't necessarily, you know, equate to a hugely monetizable one, right, or something, you know, like a Billion Dollar Unicorn. Yes, I would have loved that. That would have been in the first best outcome. The second best outcome is to one have that degree of resiliency to have survived as a business for five, six years and then survived through a pandemic and then successfully sell the business to a company that now is going to take our product and distribute what we created. It's three million plus user base. It lives on it. Maybe I'm not at the helm and my partner are not calling the shots anymore. It's it is the second best outcome. I think one could hope for as an entrepreneur. Was it some huge finacial windfall? By no means right, but you know, I think we were at a crossroads thinking through like okay, do we just keep operating independently and keep fighting the good fight, or do we take this opportunity to roll this up? We retained some part of the business,...

...hotel credits, and there's a lot of exciting stuff going on there. Then also, on a personal basis, to touch upon that, both my partner, I won't speak for her, for me specifically. You know, I was at a place where I was at a different phase of life, not necessarily just monetarily and like the fashion leads, I have a supporting a family, etcetera, etcetera, but I was doing this business for the last six years. I was ready to sort of think about what the next stage of my career was. It was a great launch pad at this transaction to sort of tie the bow on something we really cared about and have see it live on, have a remaining piece of the business keep going, so we're still doing right by a lot of our stakeholders, are investors, our staff, etcetera, and at the same time, on a personal basis, use that as an inflection point to think about what else I want to do, what's the next stage of my career? So it all sort of made sense and I'm just really proud of the team and the product and how we sort of managed through it all where, yes, we may have peeked out in two thousand and nineteen, but two thousand and twenty like we survived, and that can't be said for a lot of other travel text startups. No, that's amazing and it's so inspiring hearing you talk about, you know, from the beginning and raising capital and, you know, putting yourself on the line for your employees. Now coming full circle and have sold the business and, you know, coming through the pandemic. It's really inspirational and just hearing you talk about everything you did. I hope that our listeners are enjoying this conversation because it's so interesting and maybe people have actually seen the brand out there when they're traveling to because I know you talked about what was different from this was that the big attractions that they were looking for your kind of giving that inside knowledge, and that's from your personal experiences from traveling, from through banking. So well, Deepak, thank you so much for joining us to say and sharing your story. We have one last question before you go. So take a step away from the finances. What's the last non financial decision you've had to make recently? Recently? Yeah, we're in the middle of moving. So I'm here in Brooklyn Right now, my partner and our three yearold daughter.

We're all going to move to Los Angeles and a couple of months. The decisionmaking that's going on right now is what preschool and what neighborhood to live in Los Angeles. That's been the major topic of discussion in the household and we keep going back and forth. But it's a fun decision making process because it's exciting to think about where will end up next. That's very exciting and such such a change from where you were a year and a half ago, it sounds like. Well, best of luck with your move and and your future endeavors in your new projects here. Thank you so much for taking the time to talk with us today. We really appreciate it. Thank you for having me have a wonderful day. That was great. So I think our listeners really enjoy that. Thanks very much to Victoria and deep had for letting US listen in on their conversation. We appreciate their time and perspectives and thank you for tuning in. We hope you'll join US next time on decision dialogs for more stories from successful dosest owners along for now. Thank you for listening to decision dialogs. We hope you found today's stories helpful for your own decisionmaking. If you like to listen to more episodes, you can subscribe on your preferred podcasting APP or visit our website, where you'll also find show notes and important disclosures. WWW DOT willcom. Forward Slash decision dialogs. This has been a production of twin flames studios.

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