Alana Picov

1:01Winning at Salesforce, still unhappy

ChristianneFor some people, Salesforce is a dream job. In a lot of ways, you had won the corporate game. What did winning feel like on the inside?

AlanaIt felt amazing. I got recruited to go to the UK for a sales job. They were going to pay for me to relocate. I was like, whoa, I did it. I'm in a brand new country, they're paying me well, I have all these benefits. And in a sales job, you're measured on your quota. When I set a goal, I need to achieve it or overachieve it.

When you see that leaderboard and your name is at the top, that is the best feeling in the whole world. Every month you'd be ranked against your team, and whoever did the most sales was at the top. I would refresh that leaderboard every morning. Okay, where am I?

Winning felt like being at the top of the leaderboard, getting paid bonuses, getting praise from everyone. But what I realized is that a lot of that external validation masked the inner emptiness I had. I was getting all these awards and I was getting paid really well, and I was like, why am I still so unhappy?

It came down to not being passionate about what I was doing. Salesforce, love ya, but I don't care about APIs and integrations. That didn't get me out of bed. After three years, I realized I can get all of these promotions and awards, but do I really want to be doing this in ten years? In five years? Next year? And the answer was no.

ChristianneWhat did the unhappiness feel like?

AlanaI felt pretty lost, and honestly pretty bored. I'd commute an hour, an hour and a half. I'd sit on calls where people talked about our five-year plan, our three-year plan, and I'm like, you guys are all lying. You don't even want to be at this company in five years. I wasn't motivated by the job, and all the corporate jargon never sat well with me. I felt bored and unfulfilled.

3:25Two suitcases and a 5-floor walk-up

ChristianneI want to talk about when you first moved to New York and you were living in that SoHo walk-up. Five floors, no elevator. Where are you sitting, and what can you see?

AlanaThe good old walk-up. First of all, I didn't know everything was a walk-up in New York. That was an eye-opener. I came here with two suitcases, lugging these 50-pound suitcases up five floors. I walk into this place, no AC. I'm already dying from the stairs. And I remember closing the door and it was just quiet. New York is so loud, but in my head I was like, shit. I'm doing this. I moved here. I'm starting a company. I don't know if it's going to take off. All my friends are busy with plans, and I'm like, okay, now what? I'm not going to an office. Am I just going to work from home?

ChristianneWhen you're in that SoHo walk-up by yourself, was it fun to go to bars? Did you feel like you had something to celebrate?

AlanaI always love going out with my friends. But in the back of my head, I dreaded the small talk with new people. "So what do you do?" I'm starting a candy company. "How's that going?" Do I tell them it's so cool that I'm pursuing my life dream? Or do I tell them the real thing, which is, holy fuck, I have no idea what I'm doing? I didn't know anything about projections or supply chain or COGS or marketing. I had no idea what I was doing, but I felt like I had to pretend I did.

ChristianneWhat did you say in those situations?

Alana"Yeah, it's going great. How are you?" I'd always deflect. Everyone asks how the company is going, and it's my least favorite question, because 80% of the time something is going wrong. I put so much pressure on myself to make this work that I always want to act like everything's sorted. It's exhausting to say over and over again.

6:41The mentor call with the camera off

ChristianneSo you're in that SoHo walk-up, about to get on a call with someone who has built a hundred-million-dollar company, and your camera's off. Why?

AlanaI got on a call with one of my former mentors, who I really cared about. I was asking everyone in my network, what do you think of this idea? Give me any advice. And that walk-up was tiny. When I say shoebox, the bathroom was smaller than an airplane bathroom. I barely had a desk.

So I'm sitting on my bed with the camera off asking him, what do you think of this company? And he says, "Alana, do you want the honest truth?" Yeah, hit me with it. And he's like, "I'd think twice about doing this. The candy space is really saturated, the margins are really thin. There are a lot of factors going against you. You had a really good job." And then he says, "I'm actually going to this other company, and I have an opportunity for you."

So now I'm thinking, first of all, you don't think my company's going to work. And now I have an opportunity in front of my face that's going to pay me money, and right now I have no salary. I'm in New York, I have no idea what I'm doing, and I have no one to talk to about it, because I'm sitting on my bed in the sweltering heat freaking out.

ChristianneWhy was your camera off?

AlanaBecause I had no space to take a call from. He went off video because I was off video. Let's be equal here.

ChristianneWhen he's telling you the candy space is hard and it's going to be a brutal grind, where do you feel that in your body?

AlanaEven telling that story, I felt it in my throat. I value his opinion so much, and my friends' and family's opinions. And you always doubt yourself. Am I naive? Am I seeing something nobody else is seeing? No one had done what I was trying to describe, and I don't think he really got it. It's so hard to convey a brand new product when it's just an idea. People don't see where I see this company going a year or two out. They're judging me off this little idea I have now.

ChristianneWhen you said no to that job, did you see it as bravery, or as the only path for someone like you?

AlanaBoth. Yes, it's brave to turn down an opportunity like that. But I had already quit my job. I had one goal in mind and I was full sending it. I think you give yourself a certain time frame to fail, and you don't stretch it out. I didn't really listen to the people who told me no, because I believed in this so much. I have two co-founders who are just as committed. This is what we're doing until we either succeed or I fall flat on my face.

10:07Smiling in photos, scared behind them

ChristianneWhat's happening in this photo?

AlanaThat's so funny. This was a couple of months after I moved to New York. I was in Times Square with a friend, a real New Yorker, and she's like, "Alana, Times Square is disgusting." And I'm looking around, so excited, the flashing lights, the energy. I'm in New York, let's go.

But it's funny looking at these photos, because in the back of my mind there was so much pressure to succeed. Having lived in the UK, I can tell you New Yorkers and Americans work way harder. There's a grind-and-grit attitude here that you either adopt, or this isn't the city for you. All my friends were like, "You live in New York, you're living my dream life." And I'm like, if you actually knew how I felt behind some of these photos. You see me smiling, having the best time, and I'm freaking out. I moved my whole life here. My whole family is in Toronto, my closest friends are in Toronto, and it's just me and my co-founders trying to make this work. This city can eat you up if you're not tough. I think I'm tough, but I crack sometimes. And I'm not going to crack right now on this podcast.

ChristianneIf you were being totally transparent with the friends seeing your posts, what would you have told them?

AlanaI'm scared shitless. This is such a cool life, but I'm taking the biggest risk of my life. I could easily be at home in a corporate job, surrounded by family and friends.

Every day I wake up with anxiety. Is this going to work? In the corporate world you have everything mapped out. You have your next step, a manager to support you if things go wrong, people to fall back on. When something went wrong at Salesforce, it wasn't really my problem.

Now my two co-founders, Sabrina and Carolyn, and I have a WhatsApp group, and there are always messages: this went wrong, this went wrong, this went wrong. Now everything is my problem. I wake up every day with problems to solve. In corporate, a deal slips or a customer is upset, and it can ruin your day, but it won't ruin your career. Now everything is my problem, which is honestly a great thing, because I own this business and I'm not working toward somebody else's mission.

Corporate was a lot of work, and starting a company is a lot of work. Work doesn't scare me. I went to business school, I grinded at Salesforce. The hard part isn't the work. It's the weight that comes with it. I can't hand a problem off to the solutions engineer anymore. I can't ask my manager what to do. A customer complaint? My problem. Something wrong with the supply chain? Our problem. And sometimes I miss being able to hand my problems to somebody else.

ChristianneAnd not go on vacation and take them with you.

AlanaOr close your computer at six o'clock and have the whole night ahead with no one bugging you.

ChristianneThere's a stretch where you're working toward your launch, and friends around you are getting promoted and buying homes back in Toronto. How did that feel?

AlanaI always try to remember that comparison is the thief of joy. What a lie. We all compare ourselves. It sucked, and it still sucks. Some of my friends are buying homes, getting promotions, getting stock bonuses. Some of their companies are about to IPO and they'll be in a really good spot. And here I am trying to get candy off the ground, not knowing if it's going to work. It's still hard not to compare yourself to your friends, or to other founders in the space. They got into all these stores, why couldn't I? It takes a lot of grit and resilience to keep moving forward, and to wake up every day and say, I'm going to make this work until it doesn't. But it will.

21:45The night before the launch party

ChristianneWhat was the business actually doing when you made that launch reel?

AlanaWe were so excited. October third was the day we were supposed to have our production run. After about a year and a half working on Good Greed, it was finally being brought to life. Pre-orders would go live October third, and then October twenty-fourth was the big launch party we'd been working toward for years. We didn't have everything in place, but most things were coming together.

ChristianneSo what happened on October twenty-fourth?

AlanaThis was the day we were going to launch candy. We rented out a bar, we brought in DJs. We'd gone to the manufacturing plant three months before to make sure everything was in place, gone back and forth on samples, and everything looked good. We had friends flying in from Toronto and the UK. We were supposed to have 75 people, and the guest list was at 125.

Production always takes longer than you expect, and we were getting our product the night before the party, which was already risky. But we'd tested it, we'd tasted it, and we'd given the manufacturer everything: the taste, the feel, the texture.

So the night before, I'm sitting in my apartment with Sabrina. Carolyn was coming in the next day. We have the camera up to get the behind-the-scenes of tasting it for the first time. And Sabrina tries it, and you can see her reaction. I'm thinking she's just being dramatic. Then I taste it, and it's so sour. This is not what we planned. Okay, let's try the cherry. And the cherry is so wet and sticky. And we just look at each other.

What are we going to do? My parents are flying in, all our friends are in, the venue's booked, and we have all this product. And we were supposed to be on Pop Up Grocer shelves the next day. We'd already committed to stores.

The product was fine. It tasted good. But we have such high standards, and this was going to be the market's first impression of us. So we made the tough decision to pull it from shelves. We could have put it out. We could have reformulated with additives to make it more shelf stable. But we decided to delay the launch, take two or three months to sort it out, and relaunch in January.

That sucked. The party was still really fun, and our friends and family were so supportive. We gave all the candy out for free with a little note card: hey, we messed up, here's a discount code for when we actually launch. For a moment we were like, fuck, this sucks. And it was embarrassing.

ChristianneReally?

AlanaMy friends and family know I've been working on this for hundreds of hours, and then I show up and say, we messed up, this isn't what it was supposed to be. We could have done it quietly, taken the safe road, skipped the launch party. But you have to take risks as an entrepreneur. Full send it. If it doesn't work, we'll figure it out. Our company is never going to be perfect, but we'll always put our best foot forward.

ChristianneWhy still have the launch party?

AlanaWe'd already paid the deposit, and friends had already landed. And it was a great moment to generate buzz. We got so much content from it. We got feedback from 125 people in one room. We set up a little confession booth where people could say what they really thought. And good things happen at the most unexpected times. That video of Sabrina tasting it got 2.5 million views. I really wish we'd had our TikTok shop linked to it.

I'm really happy we waited, because the last thing I'd want is for people to think our product wasn't good after all those years of not taking shortcuts. Shit happens, and it's going to happen all the time. Just bounce back quick.

28:32Her brother, her hardest critic

ChristianneTell me about an entrepreneur in your life that you admire.

AlanaMy brother. I've always looked up to him. He's eight years older than me, and he didn't take the normal path. He dropped out of university in his first year and started businesses from there. His first was a solar development company. Now he's working on vertical farming. He's so smart, and he's always available when I have questions. We're raising money right now and have so many questions about the model and what investors look for. He has such a busy schedule, but he always makes time for us.

ChristianneWhat's your dynamic like with your brother?

AlanaWe joke around all the time. Very sarcastic. Life's not that serious with him. We'll go out together, have dinners together. But when it comes to business, we're very serious.

He bullied me when I was younger. The story my mom always tells is that when I was a baby in one of those jumpers, my brother would throw a blanket over my head and spin me around in circles. We'd play ping-pong and he'd whack the ball so hard at me. And he was really hard on me in school. My parents were never strict about academics, but my brother was the hardest person on me. If I got a ninety on a test, he'd say, "Well, Alana, you know, ten percent of the time you're a hundred percent wrong."

It annoyed the hell out of me. But I think he gave me thick skin. He's probably the reason I'm pretty tough today. I'm still soft and mushy on the inside. But I've got tough skin.

32:12Pitching Joe Jonas on the street

ChristianneA lot of entrepreneurs, myself included, need a certain level of delusion. What's the craziest thing you've done to get your mind right?

AlanaHonestly, I get a lot from other people's validation. When I tell people about this and they say it's such a good idea, I take that and run with it. I remember seeing Joe Jonas on the street in the West Village. I could have just asked for a picture or told him I'd been a fan since I was ten. But the first thing that came to mind was: pitch him. Why would I do that? This man is not a businessman. But I walked up to him and said, "Hey, I'm starting a healthy candy company. Here's the plan. Do you have any advice?"

And he said, "I think that's a great idea. I have a kid, and I think this would be perfect for them." And I'm like, it's going to work. Joe Jonas told me it's going to work. I didn't even ask him if he wanted to be recorded, so I'm so sorry, Joe. But he was excited about it. In moments like that, I'm pretty delusional. But I don't mind walking up to people and asking.

33:37What she knows now

ChristianneWhat do you know now that you couldn't have known sitting in that tiny SoHo shoebox?

AlanaYou're never going to have all the information you need to make a decision. I could have kept talking to my mentor, trying to gather everything. But you're never going to be ready. There's never a time when you have all the facts, all the data, all the resources. You just need to do it. You need to move to a country without knowing if your business will work. You need to place that order for twenty thousand bags without knowing if you can sell them all.

I used to look at entrepreneurs and wonder where they got their confidence. People ask me that now: how are you so confident about this? And the more I'm into it, the more I realize it isn't confidence. It's being okay with tolerating uncertainty. Being okay with not having all the answers. That's so much easier to say than do. Even as I say it, there's so much I'm freaking out about because I don't have the answers. But you take the information in front of you, make the best decision you can, and move on, because it's not going to be perfect.

ChristianneIf you could tape one sentence to the wall of every founder's apartment, not a motivational quote but something true they need to hear every day, what would it be?

AlanaIt's not that deep. You can get so caught up in the little things that they ruin your day. My old manager used to work for Red Bull, and he'd say, "At the end of the day, we're just selling sugary water." Obviously you need to care about your business, your product, your customers. But it's not that deep. Life's short. If things go right, great. If they go wrong, it's not that deep. Have fun with what you're doing, do it right, and be nice to people.

ChristianneAlana, thank you so much for joining us.

AlanaThank you for having me. This was so much fun.