LISA CHOW: From Gimlet Media, I’m Lisa Chow. This is Startup, the show about what it’s really like to start a business.
One thing that's become clear to me in my reporting on startups is this: being a founder can be pretty isolating.
You’re responsible for people’s livelihoods. There’s this pressure to act like you always have everything under control. And, a lot of times, your friends and family can’t relate to what you’re going through. It’s hard to lean on them for support, so you need someone else to turn to. Some founders have mentors and advisors, and others go to people like Jerry Colonna.
Jerry is an executive coach, but he’s also worked as a venture capitalist. You might have heard him on our show before. In one episode, he coached our very own Alex Blumberg. A lot of listeners really responded to that episode, so we decided to ask other founders if they wanted to talk to Jerry. That’s when we got this call.

JASEN YANG: Hi, my name is Jasen Yang, and I’m the founder and CEO of Polly Portfolio. We’re a three-year-old company that works in the investing software space.

LISA: Jasen’s company is called Polly Portfolio. They make software that helps people decide how to invest, and, to get the company off the ground, Jasen took some big financial risks. He left a high paying Wall Street job. He stopped taking a salary, and he invested some of his own savings into the business.
And he did this while his wife Lynn was taking care of their two young kids full time. It’s now been three years since Jasen started his company. He’s still not taking a salary. And living in New York City hasn’t helped either. He and his wife have ended up spending a lot more than they expected. Jasen told us that they’ve had to make sacrifices—some that will affect their family in a big way.

JASEN: We've made the decision to sell our apartment, and I think, that is while I can rationalize that, I don't particularly want to do it and neither does my wife and I think that's creating some resentment for both her and me. I kind of want to show to my wife and my family that the sacrifices we made were worth it.

LISA: That’s why we put him in touch with Jerry.

JERRY COLONNA: Well why don’t we get started and...how are you and more important what would be helpful to talk through?

LISA: Jasen says it’s stressful to ask his wife to give up their home so that he can stay focused on his startup, especially because when he first reached out to us, his wife was pregnant with their third child. At times, the anxiety is so powerful, it’s prevented him from talking to Lynn about big decisions they have to make. Like where will they live? And what schools will the kids go to? He finds himself clamming up, and becoming defensive.

JASEN: you know I think I feel guilty about having brought my family along on this trip. And I feel kind of resentment about the situation that I hate to be in where I ask someone to trust me on because I'm me rather than on the merits of…

JERRY: Just to have faith in you

JASEN: Yeah.

JASEN: My natural mechanism is to go to my wife and try to get her to see the situation on its own merits. See what I saw in it. See what my investors saw in it.

JERRY: That's your instinct.

JASEN: That's my instinct. I have an instinct to go and pitch her the way I pitched the investors and the team.

JERRY: Ok. But there's a part of you that says that may not be the right way.

JASEN: Yes.

JERRY: OK. I agree with you and the hint is in two words. The first word you use is in the phrase "get her to." You hear that?

JASEN: Yeah.

JERRY: The second word was pitch.

JASEN: Right.

JERRY: You literally said pitch your wife.

JASEN: Yeah.

JERRY: Ok

JERRY: What's missing in your imagined dialogue with your wife. Hint, it's not a pitch.

JASEN: One thing that's missing is how she feels.

JERRY: That's one. What's another one.

JASEN: Um…

JERRY: Whose other feelings are missing?

JASEN: Oh my feelings.

JERRY: Oh my feelings.

JASEN: Right.

JERRY: Part of the construct that you feel really conflicted about is that you've made a decision that affects your wife. Now, I'm sure there were times where there are conversations she may have even said, you know honey don't worry about it. I've got it. But as time has passed and you've not sold this company for a billion dollars to Google and retired off to the sunset. What's missing perhaps is honest conversation and dialogue. Where you hear her feelings by sharing your feelings and run the risk of hearing her say something that might hurt you.

JERRY: There's no getting her to believe something. There is collaborating, co-creating your future together.

JASEN: Right. There's a thing about me where I hate saying to someone, “trust me.” Like that's not a thing I like to say.

JERRY: You'd rather they just know that you're trustworthy by way of your actions and your conduct.

JASEN: Exactly. Exactly. But in this case you know with Lynn,I really did ask her to trust me.

LISA: At this point in the conversation, Jasen felt like he hit on a core problem in his life. This anxiety around asking people to trust him, it’s something he’s felt a lot. Jerry wanted to drill down on that, and understand what's behind it.

JASEN: When I think about asking someone to have faith in me, there's this block, you know it literally feels like there's a quarter of a brick just stuck inside my chest.

JERRY: A quarter of a brick.

JASEN: Of one of the little construction bricks.

JERRY: It's like it's like it's like lodged.

JASEN: Yeah and it's about two inches wide and three inches long and it makes me not want to breathe. It makes me want to lie down. You know, I feel my body telling me not to say that.

JERRY: Yeah.

JASEN: Not to say those words. Trust me. I mean it's a pretty mortal fear....you know I suddenly thought of something.

JERRY: Good.

JASEN: So I was digging around my house a few months ago and I found this USB drive from my old computer. And I found this journal entry...I didn't, I was not in the habit of writing as a kid. I wrote this seven page long tirade about something that had happened when I was in high school and what had happened is that I had lied to my mother. I had told her that I did this paper and I hadn't and then I eventually had to fess up and then we had this massive fight. Enough that you know as a 15-year-old or 14-year-old I wrote seven pages of single spaced you know to evaluate my feelings and I felt like it was really you know even in that journal entry I admitted shame about it.

JERRY: Yeah.

JASEN: I was very ashamed for lying to her.

JERRY: What did she say to you?

JASEN: It was couched in the language of you know the only thing you need to do is to be honest. And what kind of person lies to their mother.

JERRY: Ah.

JASEN: Right.

JERRY: What kind of child lies to their mother? How can I believe you if you lie to me.

JERRY: Am I hitting close.

JASEN: Yeah. It's a pretty intense feeling.

JERRY: Yeah.

JASEN: And I kind of understand that well maybe that's why I don’t like to ask people to trust me.

JASEN: You know…

JERRY: Is this is the first time your mother made clear to you that.

JASEN: Far from it.

LISA: Jasen says that growing up, there was a lot of pressure in his home. His parents had immigrated from Taiwan, and they had high expectations of him and his brother. They also demanded a lot of respect from their kids. And what that meant was: you don’t disobey us, you should work really hard, and definitely, you shouldn’t ever lie to us.
And that last idea, Jasen absorbed so much so that today, as an adult, he tries to never say things that could later turn out to be untrue. And that's actually a pretty hard rule to live by, especially as an entrepreneur, because the future of a startup is so hard to predict.

Jasen and Jerry started talking about that fear of lying, and why it took hold in such a profound way when Jasen was younger.

JERRY: Yeah. So as children, okay, we’re organized around seeking three principal things: to love and be loved.

JASEN: Right.

JERRY: To feel safe and to feel a sense of belonging. Shame threatens all three. That's why the half a brick in your chest feels mortal. Feels deadly. Because banishment from the family is the equivalent of death to a child. Right.

JASEN: Right.

JERRY: And one of the preconditions in order to belong according to Mom was to never be lied to. Or to experience an untruth.

JASEN: Right.

JERRY: You've done this very sophisticated maneuver, which is: if I don't promise you anything, then I can’t experience the pain of having disappointed you. It's actually a brilliant survival move.

JASEN: Right. I mean to me it feels like honesty, but I think you're also right. It's a survival mechanism. You know, so that is for me almost 25 years ago. And yet these feelings about not asking someone to believe in me. But you make the judgment, right. Statements of fact. That's still the mode that feels comfortable.

JERRY: Because you're not asking them to—

JASEN: Believe me.

JERRY: Believe you.

LISA: After the break, we'll pick up Jasen and Jerry's conversation, when we'll find out that Jasen's need to be 100% truthful also threatens his business.

<<BREAK>>

LISA: Welcome back to Startup.
Before the break, Jasen and Jerry were working through Jasen's problem: his difficulty asking people to trust him. It was causing tension in his relationship with his wife, and as it turns out, it was also creating a problem for his company—especially when he had to go out and pitch investors. He told Jerry about one time in particular.

JASEN: You know about a year and a half ago I went out to raise more money for the company. So we had done a seed round, we had build a product. We were still waiting to see how it was going to work out. And I was getting ready to go hop on a plane to California and go beg for some money. And I felt awful, like to the point I thought I was sick. And then like I was nauseous, I didn't eat all weekend before I got on the plane.

JERRY: Pit in the bottom of your stomach?

JASEN: Yes. And then for me the way that cleared up is I realized that I was putting pressure on myself to sell a business when all I had was a product and I said well just tell them what we've done right. I'm not going to make any promises about what the business is. I'll just show them the product that we have and then I was able to go out and you know have three days of meetings and not feel sick and have really enjoyable meetings. However, you know I didn't achieve my original goal. I was out there to try to raise myself a Series A, and the way I pitched it, they were like okay, well, it didn't quite seem like you're ready for your Series A yet. And you know look I don't know that it would have done anything differently or I should have done anything differently. But I also know that my decision not to try to make promises about the business certainly didn't help my cause.

JERRY: Right. And how's fundraising going for you.

JASEN: Um. Well...mixed.

JERRY: Okay. So I have an idea. Having been an investor, I'm going to say something to you now that's going to be really uncomfortable. Early stage investors invest in people. They bet the rider as much if not more than the horse. When you invest at the seed and Series A level. You're not investing in a product

JASEN: Right.

JERRY: You're not even investing in a business. They don't even invest in the idea. The idea is a hook. It's the thing that draws people in. It's the opportunity. That's why investors will stay with a company even as it pivots to new ideas, because they believe in that person. Does this land for you?

JASEN: Sure. I've spent my whole career in investing in various sorts and I know I.

JERRY: You know the truth of what I'm saying.

JASEN: Right, well I've gotten pitches, right. And when someone walks in and says, “Trust me,” I can feel myself as a human sort of responding to that. And so I know—

JERRY: And you either do or you don't.

JASEN: You do or you don't.

JERRY: Right. And your childhood survival strategy leads you to sort of be in this place of you know, you better stay away from that trip wire of being over promising.

JASEN: Right. I think that's absolutely right. And I'm certain that means that when I go to fundraise, my ask doesn't seem as strong as some other folks’.

JERRY: What is the honest stance to take with a potential investor. How much money do you need?

JASEN: We're determining our strategy.

JERRY: Okay. Good. Good answer. I like that equivocation. Okay. But let's imagine for a minute it's a couple of million dollars.

JASEN: Yeah.

JERRY: Here's the product, here's a service, here's what we've built so far. We need $3 million. Take your seat. CEO.

JASEN: But they should see that I have...you know, I think, and now I'm on that line between evidence and belief.

JERRY: Jasen, do you know what you're doing?

JASEN: Yes. Not only I know what I'm doing. I know the domain. I'm a great leader. I think. I know how to run a business. I know how to build a relationship. I know how to sell.

JERRY: Is there a market opportunity here?

JASEN: There's a great market opportunity.

JERRY: Is there a tremendous need?

JASEN: There is a tremendous need. We were ahead of our time.

JERRY: What is the only thing you don't know?

JASEN: How long it will take.

JERRY: Exactly. So what. So notice what we just shifted. When I when I said, “Do you know this market,” your whole body language shifted. That's not over promising. That's stating what is true.

JASEN: Right.

JERRY: So ask me again for three million dollars.

JASEN: Well…we're building an incredible. I'm starting to laugh. But...we're building this business. We're building, We're changing the way that information in the investing world is supposed to be connected to the end investor. And look, the market's coming to us now right. We've been at this for three years. The product’s basically done. We just need to build the sales organization now that we're actually getting in-bounds for exactly the thing that we do.

JERRY: Ask me to invest.

JASEN: I guess what I would say—to achieve the milestones—oof now now I'm getting nervous right. The actual ask. Right. Like of course, you can see that well, with these $3 million, look what we can accomplish. We need cap—but we do need capital and runway to...

JERRY: If you had to capital could you do this.

JASEN: Yeah.

JERRY: No promises, but do you believe in you. That's what you want to be telling them. Tell me.

JASEN: I know that I, that we're the right team to build this.

JERRY: There you go. Right market, right solution, right time. Finally.

JASEN: Finally.

JERRY: Right team.

JASEN: Yeah.

JERRY: Would you like to join in this investment.? You want to come along for the ride?

JASEN: Yeah.

JERRY: It's going to be a hell of a ride ain't it.

JASEN: It's going to be transformational.

JERRY: There we go.

LISA: So Jasen was starting to feel more confident about his pitch. But remember, that wasn't the main thing he'd come to Jerry to talk about.

JERRY: And now we're going to go to your wife who we left off to the side.

JERRY: What would you say to Lynn. Today. Honestly. What does your heart want to say.

JASEN: My heart wants—It just wants acceptance and sympathy. I think that's what I'm looking for.

JERRY: And maybe a little understanding.

JASEN: Right.

JERRY: So why don't you ask Lynn for that right now. Lynn.

JASEN: Lynn, I I want you to understand how there's nothing more important to me than our marriage and our family. And whatever adventures I undertake in my professional life, you need to know that I feel every sacrifice that I ask you to make.

JERRY: And so therefore how do you feel about her.

JASEN: That there's—well that I love her and that there's nothing more important to me than our relationship.

JERRY: This is a good time to slip in a little thank you.

JASEN: That's true too. That's true too.

JERRY: How does it feel getting to that spot. How's that half a brick?

JASEN: It feels like it's melting. It's much more jolly rancher sized now. It's not quite gone, because I haven’t actually talked to her.

JERRY: Right. So a couple of other things to consider. Might help for her to know that you carry this guilt and resentment. It might help her to understand that it's hard for you and you know it's hard for her. Give her some agency. Ask her what she might need.

JASEN: Right.

JERRY: There's an opportunity here to use this as a dialogue as an opening.

JASEN: Right.

LISA: After Jasen and Jerry met, I invited Jasen into the studio to talk about this session with Jerry. He said he was a bit shaken afterward, but that it also gave him some clarity. It helped him understand why he’d been feeling so anxious. And so I wanted to know if this new awareness was affecting the way he was communicating with Lynn.

LISA: Can you tell me about what you went home to like the conversation with your wife… like after that session. What was it like.

JASEN: So I wasn't ready to talk about it right away. So it probably wasn't for four or five days before we had a chance to have a conversation. And it wasn't a fairy tale ending. The way I started it is I said...I said, you know, we actually never got to talk about the coaching session. You know, it was really like, I was really moved. And I kind of said like it really affected me. I tried to lay out that I had felt all this guilt around having asked her to trust me and that I think I probably have this complex about asking people to trust me. Her initial reaction was like, OK. So what are we going to do. She was not very sympathetic about it. But I mean, obviously, you know she's going through her own set of stressors. And so her reaction was like, “Okay, I guess I kind of know what you're saying. But like how does this help us sort of make decisions going forward.”

LISA: So, Jasen didn’t quite get the response he was hoping for, but it did open up a conversation about how he and Lynn were feeling. Before the session, he and Lynn had avoided talking about how the company was affecting their lives. Or when they did talk, the conversations were awkward and painful, and he’d struggle to get the language right. But after the session, Jasen said he noticed a shift in how they were working through problems together, for example selling their apartment.

JASEN: Well, we talked about you know us putting our place on the market right. And it's not something that we're doing without regret, even if this is the right thing to do. At times she might say to me, “I really hate that we're doing this.” And you know my reaction would alternate between, “Yes dear and you're absolutely right,” to, “Buck up. This is life. Get over it.” Neither of which are what you need from a partner, right? So after I kind of got away from that feeling of guilt and resentment around this, I can kind of say, the way I feel is not all negative. It's actually, okay well what about the exciting opportunities that are ahead of us right. You know maybe we'll get excited about living in a different place. Maybe we'll just get excited about like selling the place and having some cash in our bank account. And I think my ability to be positive and genuinely positive rather than guilt-ridden and resentful was just kind of the first step in sort of making it better.

LISA: And how has she responded to it. Like when you when you have kind of instead of just, buck up or yes dear.

JASEN: Well, I think it's still a process. But I think, but I think she's responded better. The tone of the conversations and sort of the back and forth has got a lot more substantive and that's kind of gotten us back to the place where you kind of want to be, which is that you’re partners in this journey.

LISA: So Jasen feels he and Lynn are making gradual progress. As far as pitching his business goes, he’s seen a big change in the way he approaches it.

LISA: You had described that fear of asking someone to trust you. You described it as a brick lodged in your chest.

JASEN: Yeah.

LISA: And I'm wondering, does it still feel like that?

JASEN: No. I've mean somehow that brick has kind of been dissolved, maybe it was that perspective of being like why wouldn't I ask someone to trust me. Right. You know especially ‘cause I'm asking them to trust me to do something that I know all about. And I'm kind of pretty uniquely qualified for it. Well geez that was silly for me to feel nervous about. And I think when it comes to talking about myself in the context of the company, you know, some of the things that made me tight in the chest have completely gone away.

LISA: Jasen Yang is the CEO of Polly Portfolio.
Jerry Colonna is an executive coach and also host of The Reboot Podcast.
Since his session with Jerry, Jasen is still pitching his company—but this time he's doing something that might make his family’s life a bit more stable—he's looking to get acquired.

StartUp is hosted by me, Lisa Chow. Our show is produced by Bruce Wallace, Luke Malone, Simone Polanen, Emanuele Berry, and Amy Standen. Our senior producer is Molly Messick. We are edited by Pat Walters and Annie-Rose Strasser. Production assistance and fact checking by Max Gibson.
Mark Phillips wrote and performed our theme song. Build Buildings wrote and performed our special ad music.
Additional music by the lightning fast Bobby Lord. For full music credits, visit our website. David Herman mixed the episode.

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