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When to seek advice and when to ignore it


Smart entrepreneurs know one of the secrets to scale is leveraging wisdom from others. (In fact, that’s the mission of this show!) But not all advice is right for you right now — and some can even be disastrous. As the founder of the proto-fintech platform LearnVest, Alexa von Tobel scaled her business by seeking advice from mentors and friends … and then, taking only the advice that served her mission. Following Alexa’s story, you’ll learn how to become a good advice detective, with the power to sort the transformative advice from the traps.

“What I’ve learned in my, now, almost four decades on this planet is that trust is the most important thing, period.”

— Alexa von Tobel
About the guest:

Alexa von Tobel is the co-founder and managing partner of the early-stage investment firm Inspired Capital. Previously, Alexa founded LearnVest in 2008 with the goal of helping people make progress on their money. After raising nearly $75 million in venture capital, LearnVest was acquired by Northwestern Mutual in May 2015 in one of the biggest fintech acquisitions of the decade. Following the acquisition, von Tobel joined the management team of Northwestern Mutual as the company’s first-ever Chief Digital Officer. She later assumed the role of Chief Innovation Officer, through which she oversaw Northwestern Mutual’s venture arm.
About the host:

Reid Hoffman is the host of Masters of Scale. A Silicon Valley entrepreneur and investor, he’s known for his spot-on insights on how to scale a startup. He’s a partner at Greylock and co-founder of LinkedIn, and co-author of the best-selling Blitzscaling and The Startup of You.

Also featured in this episode:

Jack Conte is the CEO and co-founder of Patreon, a company whose mission is to “change the way art is valued.” A multi-instrumentalist, singer-songwriter,…

Phaedra Ellis-Lamkins is the co-founder and CEO of Promise, a gov-tech start-up that creates flexible payment solution — and counts Jay-Z’s Roc Nation among…

Saeju Jeong is the CEO and co-founder of Noom, the app that matches its millions of users with coaches to help achieve their fitness, …

Cindy Mi is the founder and CEO of VIPKid, an education technology company that connects a global community of English-language learners with the world’s …

Dan Savage is an author, sex-advice columnist, podcaster, pundit, and public speaker. For more than 30 years, he has written the sex and relationship …

As the CTO of Motorola and then of Cisco, Padmasree Warrior led innovative engineering teams at massive companies — she’s a leader behind Motorola’s…

I believe gathering advice is one of an entrepreneur’s most valuable skills — but so is ignoring advice.

— Reid Hoffman
Transcript of Masters of Scale: When to seek advice and when to ignore it

Dan Savage on his advice column Savage Love

DAN SAVAGE: How did I get into the advice racket? By accident. I met somebody who was about to start a newspaper at a party, and I said, “Oh, you should have an advice column because everybody reads those. You see that Q&A format, and you can’t not read it.”

And he looked at me and said, “Excellent advice, please write the advice column.”

REID HOFFMAN: That’s Dan Savage. For more than 30 years, he’s written the sex and relationship advice column, Savage Love. His advice also comes in the podcast form, in the long-running show Savage Lovecast. Dan is an advice-giving all-star. But when he started, he made a point of not calling himself an expert. 

SAVAGE: One of the first things that I heard was: what qualifications do you have? And I have none, zero, except the only one you really need to give advice. You look up advice in the dictionary, and it says opinion about what could or should be done. The only qualification you need to give someone your opinion is they asked for it.

HOFFMAN: In fact, Dan asks for his audience’s opinions too. And he’s made their responses a pillar of Savage Love

SAVAGE: The advice column was always a debate between the author of the column and their readers, so half the mail was people saying, “You’re right, you’re wrong. You missed this thing, you should have said that.” And half my columns were those kinds of conversations.

HOFFMAN: These conversations drive home one of the professional hazards of giving advice. Dan knows his words of wisdom won’t always be taken, and they won’t always be right. 

SAVAGE: As an advice columnist, you’re always operating with half the story. I have given advice to someone and then the person that they were writing in about saw the letter from their partner in my column and then wrote me to tell me the other side of the story, which made my advice inoperative or incomplete. You really have to think hard about what you haven’t been told.

HOFFMAN: Ultimately, what Dan hopes his audience knows is that his advice is rarely a simple directive.

SAVAGE: A lot of people who yell at me operate with this assumption that advice is binding arbitration, that this person has to do what I told them to do, and what if I told them to do the wrong thing? Well, that person gets to make their own choice, ultimately. And they’re just going to take what I had to say into consideration.

HOFFMAN: Exactly. That’s also true when it comes to seeking advice as an entrepreneur. Collecting wisdom from colleagues, mentors, and friends is one of the best ways to accelerate your learning. But only if you listen with a critical ear.

That’s why I believe gathering advice is one of an entrepreneur’s most valuable skills — but so is ignoring advice. Not all good advice is right for you right now, and not all bad advice will be bad forever. The key is tapping into the right advice at the right moment.


The profound effects that advice has on your entrepreneurial journey

HOFFMAN: I’m Reid Hoffman, cofounder of LinkedIn, partner at Greylock, and your host. And I believe that gathering advice is one of an entrepreneur’s most valuable skills — but so is ignoring advice. Not all good advice is right for you right now, and not all bad advice will be bad forever. The key is tapping into the right advice at the right moment.

I’m going to ask you two questions. Ready? 

First, what’s the best advice you’ve ever received, and who gave it to you? I’ll give you a moment to think.

Got it? Good. Now, what’s the worst advice you’ve ever gotten? Again, think about who gave it to you, and whether you followed its twisted path.

Both good and bad advice can have a profound effect on your entrepreneurial journey. The right nugget of wisdom given at the right time can transform your perspective and reveal your blindspots. (In fact, that’s the very mission of this show!). 

But the wrong advice at the wrong moment can be just as impactful. So you need to develop not just the habit of seeking out advice, but also, how to notice when what you’ve been given isn’t useful, and thus can be politely ignored.

I wanted to ask Alexa von Tobel about this because as the founder and former CEO of LearnVest, Alexa built her career bringing much-needed financial advice to the so-called 99%. Founded in 2008, LearnVest was a proto-fintech platform that offered money management resources — from budgeting bootcamps, to spending trackers, to consultations with human financial planners. When they were acquired by Northwestern Mutual in 2015, it was a clear sign that the fintech era had arrived.

Alexa herself is also an author of two bestselling books on financial advice. And as co-founder and managing partner of the early-stage fund, Inspired Capital, Alexa is now advising and mentoring a new generation of entrepreneurs. 

Alexa’s success came not only from her relentless pursuit of wisdom from mentors but also an ability to shed advice that might have led her astray. So to help us hone our good advice detectors, we’re going to hear not only from Alexa, but from other Masters of Scale guests who can share the advice that has most shaped their careers.

One early bit of valued guidance Alexa von Tobel received was from her father. And it had to do with the topic of advice itself.

ALEXA von TOBEL: My dad was a specialist, a behavioral pediatrician who took care of very complicated children. And he always said every other human has something beautiful to teach you. So your job, whenever you meet anybody, is to figure out what they can teach you.

HOFFMAN: This advice resonated with Alexa in the moment. But it took on special meaning after her family suffered a terrible loss. 

von TOBEL: So when I was 14, my dad unexpectedly passed away, and I have two older brothers, and my mother, she’s a pediatric nurse practitioner. Overnight she became a single mom. I remember in that 48-hour window, my mom was like, “Oh my goodness, I have to think about our finances and get all of that in shape.” 

HOFFMAN: Watching her mother untangle the family finances was formative for Alexa. And even through her grief, she recognized that there was something she could learn.

von TOBEL: As a child, it’s literally your worst nightmare to lose your parent. That is the thing you’re most fearful about. It’s why every children’s book has it at the start. I just remember there was a moment in my head where I was like, “I’ve already had the worst thing that could happen to me happen, and life is really short.” And I just had this very clear prism of: you get to do it once and in a matter of seconds everything can change. 

It kind of gave me this courage to not really care that much about what everyone else is doing and what everyone else thinks. Maybe a beautiful way to think about it is actually a real gift that my dad gave me.

HOFFMAN: Yeah, how you convert challenges and difficulties and opportunities is an essential entrepreneurial skill and an essential life skill.

HOFFMAN: This gift Alexa speaks of gave her the freedom to make decisions outside of other people’s opinions. And she took this fearlessness into her early career as a trader at Morgan Stanley. But there, she got a front-row seat to the fallout from bad advice given confidently. 

Alexa von Tobel on experiencing “The Big Short” first-hand

von TOBEL: Morgan Stanley’s prop desk, their internal hedge fund, ended up hiring me. And Reid, that was the desk where The Big Short happened. I came to work one day, and there were security guards, and I remember thinking to myself, “This doesn’t seem like a normal day of work.”

HOFFMAN: The Big Short, of course, refers to the true story of traders betting against the housing market, making record profits by going against established wisdom. But it would also lead to the third largest trading loss in history at the firm. 

von TOBEL: I didn’t get fired because I was so young and inexpensive comparatively, and so nights and weekends started thinking about the thing I wished I could build.

HOFFMAN: Alexa’s wish was for a platform that could be a source for good, solid advice about money. It was the kind of tool she wished her mom could have had in the aftermath of her father’s death. 

It was also something Alexa felt had been missing from her own life, and the lives of her friends.

von TOBEL: I started thinking about, why don’t we get taught about our wallet? It’s a life skill like brushing your teeth. You literally need money every day of your life for literally everything, and it never goes away. You need it actually to the end. And I remember being like, “I can’t believe that this isn’t a class; it’s not taught anywhere.”

I’m sitting at Morgan Stanley, I’m finally making real money, and I remember being like, “Nobody wants to manage my money.” Even though I’m hopefully a high potential human, I’m sitting here, 22 years old with a few thousand dollars, and where do I go? Where does everyone go under the age of 30? Financial planning shouldn’t be a luxury product. It should be a product for everybody.

HOFFMAN: Alexa couldn’t stop thinking about the irony that often the people most in need of advice have the least regular access to it. 

For evidence of that, she needed to look no further than the swift collapse of the housing market. Families were steered towards subprime mortgages, following advice given with total confidence only to watch their interest rates skyrocket, leading them into foreclosure. It was a grim demonstration that bad advice is given with as much conviction as good advice. And the motivations of the advisors matter. 

Alexa left Morgan Stanley in 2008 to pursue her MBA at Harvard Business School. Soon after, the dominoes from the subprime lending crisis started to fall. 

The origin story behind LearnVest

von TOBEL: I was literally on an elliptical machine, and a good friend of mine called and was like, “I just got laid off from Lehman Brothers, I don’t know what I’m going to do. I don’t know how to pay for my rent.” And I just was like, “This is the moment.”

HOFFMAN: Alexa was in business school for only about 90 days when she decided she had to leave. The advice she received from friends was swift. Many thought it was a bad idea. 

von TOBEL: One of my best friends sat me down and was like, “Alexa, you have this fabulous trajectory, you’ve always done things well, you’re going to throw it all away.” And I remember being like, “If I don’t get this company out of my head, I won’t be able to do anything else.”

HOFFMAN: Under ordinary circumstances, advice coming from a trusted friend with good intentions, seems like the kind of advice you’re just supposed to take. 

But Alexa didn’t. And she was right not to. 

Here’s how she knew. First, she was self aware in that moment. She knew how strong her own drive was to start her business now. 

Second, Alexa saw something in the ecosystem her friend didn’t — and it had to do with timing. In a moment of total financial upheaval, a platform that would help people navigate their own finances was uniquely suited to the moment. And what seemed dangerous to her friend seemed to Alexa like a window of opportunity. We talked about this during our interview. 

HOFFMAN: Usually when I give talks at business schools, one of the things I say is two negative factors that need to be explained away: one is a background in management consulting, the other one is an MBA for entrepreneurship and investing in entrepreneurship. But you are the perfect example of how the counterexample works because you went in the MBA because you’re serious about business and want to learn. And then you went, “The time is now, I’m dropping out. I’m not going to complete the MBA, I’m going to go do the entrepreneurial thing.”

von TOBEL: Yeah. Reid, that’s right, which is, timing is everything in life. 

HOFFMAN: Of course, the timing of her exit from business school cut both ways. It was a unique moment to surface the need for accessible financial planning. But, it was still the beginning of a global recession — not the easiest time to start a company. 

von TOBEL: I took a five-year leave of absence, moved to New York. I put in all of the savings that I had, which in the rear view mirror is not a great financial planning decision. Because in New York City at that time, this was December of 2008, Reid, there were no angel funds. There was one angel group that if, if, if they invested, gave you $25,000, which as you know, pays for an engineer for a month and a half?

There was no Lean Startup, there was no early playbook. It was so early that you would learn from finding other people, other peers a good three to four years ahead of you and say, “Can you teach me what I need to know?”

HOFFMAN: This act of reaching out to peers may feel slow and unscientific. But it’s also a critical lever for getting advice that counts. It’s something I counsel all the entrepreneurs I work with to do. 

More specifically, I advise them to ask, “What’s wrong with my idea? What am I missing?” And then, they should take that question to every smart person they know. Not because every smart person they know will be right. (They won’t be!) But if you ask enough peers enough questions, you’ll start hearing them raise the same issues over and over, which will point out where you have blind spots. 

This is also a way to immunize yourself against a single piece of bad advice. The more people you consult, the more you can separate the signal from the noise.

This cast-a-wide-net approach that Alexa applied to gathering advice also worked, as it turned out, for fundraising.

von TOBEL: I talked to, honestly, anyone who would talk to me. So that often looked like 12 meetings a day, running around New York, bringing coffee to anybody. And it quickly started looking like somebody saying, “You’re nuts, I’m going to give you 25K.” And somebody else being like, “I’ll give you 10K.” And before you knew it, I actually had a little pocket of $500,000 — the people who decided to bet on me. 

HOFFMAN: Alexa used these funds to hire engineers that could build the framework of her financial literacy platform. But as the money trickled in, she still needed to tackle the substance. The site needed rich content, with advice her customers could have faith in.

von TOBEL: I had to become an expert. So I’m now a certified financial planner. I passed all the financial planning exams, but I did that because I couldn’t afford to hire somebody else so I actually had to figure out how to do it myself. 

HOFFMAN: Once she had built the website, written the content, and gone through the legal and compliance check required of a financial advisory service, she soon had her minimum viable product. She called it LearnVest — a portmanteau of learn, earn, and invest.

von TOBEL: There was always a clear plan to do content, tools, and then advice, to become the most transparent, trusted, safe place to help people manage their wallet. The content is how we turned on the company.

We built the first cash-flow-based financial planning software with a bunch of patents, and we built it from scratch. And it was really hard, because your engineers needed to understand accounting, and your product managers needed to also understand financial planning. So we had to build it all. 

HOFFMAN: With LearnVest, Alexa was helping create a category that hadn’t yet been fully defined.

von TOBEL: Fintech wasn’t a category yet, Reid. Literally the word fintech had not been used.

HOFFMAN: Technically, the word fintech was coined in the ‘90s, but back then it referred to the technology that helped financial processes. It wasn’t yet a consumer category, and most banking wasn’t done online.

Alexa von Tobel on launching their closed beta at the TechCrunch 50 conference

And maybe that’s why Alexa encountered the next speed bump in her road to scale. It was September 2009, and LearnVest had been invited to launch their closed beta at the TechCrunch 50 conference. Alexa can set the scene.

von TOBEL: They fly you out, you get to get on stage, 3,000 people, and by being selected, it’s because you’re one of the best and biggest ideas. And so you get to go on stage and present. And I was so nervous. I had emailed everyone I could think of to be like, “We’re going to launch the business. Come watch it. It’s going to be livestreamed.” So all my family, all my friends are watching from afar. 

I get on stage, and I start talking about how the future of the wallet’s going to come online. It’s going to be on your phone. You’re going to have access to advice. There’s going to be gamification. You’re going to be able to — almost in a way that doesn’t feel like work — learn and interact with your money.

In my head I’m like, “I’m going to win an award.” 

The panel of judges, Reid, were like, “This is the worst idea I’ve ever heard.” They shredded the idea live, and basically said, people aren’t going to trust bringing their money online. The gamification just seems stupid. No one’s going to be interested. The primal brain in my head was like, “Oh my god. This was not how this was supposed to go.”

HOFFMAN: Alexa had hoped for some constructive advice, or perhaps admiration and more investment. Instead, the advice she got was, “Maybe don’t bother.”

Alexa defended her idea to the judges and the assembled crowd. 

von TOBEL: I just sat there and was like, “Well, first of all, 80% of the country lives paycheck to paycheck. Nobody has money. Retirement, we’re going to live an extra decade longer, is a massive problem for the country. We have to figure it out.” And I kind of just went into all of the work I had already done and spewed it out of my brain, and ended up getting a standing ovation. People were clapping, which was great, but I got off the stage, went into a closet, and literally started bawling. And called my boyfriend, who’s now my husband, Cliff, and I was like, “I don’t know what just happened, but they hate the company. They hate the idea. It wasn’t TechCrunch, it was TechPunch. I literally got TechPunched.”

HOFFMAN: If you’re cringing on Alexa’s behalf, you’re not alone. We’ve all experienced some version of being “TechPunched,” even if it didn’t happen on a stage. Because most of us have been on the receiving end of totally devastating advice. 

For my own parallel example, I often point to when my fellow partner at Greylock, board member of Linkedin, David Sze, took apart my decision to invest in Airbnb. He said, “Well, every venture capitalist has to have a deal that they fail on in order to learn. Airbnb can be yours.” (To David’s own insight and credit, he revisited this opinion six months later.)

But whether they turn out to be right or wrong, these moments can sting when they’re coming from someone you trust. We said earlier that it’s good practice to ask smart people what’s wrong with your idea. But then of course, you have to be ready for them to tell you! 

That’s exactly what happened to another past Masters of Scale guest, Jack Conte of Patreon. What you’re about to hear is from the Lightning Round series of questions that come at the end of every interview. (If you’re a subscriber, and you listen to our complete episodes, you’ll already be familiar.)

The best piece of advice Patreon’s Jack Conte ever received

HOFFMAN: What’s the best single piece of advice you ever received, and who gave it to you?


HOFFMAN: Saar was an early investor in Patreon, and sits on their board. And it was after an early board meeting that our scene is set. 

CONTE: After a board meeting 8 years ago, one of the first Patreon board meetings. Hard board meeting. I’m a new CEO trying to figure out how to manage a board, listening to the board, taking notes, trying to figure out, what’s the overlap of all these opinions? I’m listening to the whole board meeting, writing things down. At the end, Saar sits down with me and says, “Jack, you’re just going to sit there and take notes from the board? What do you think that makes us think of your leadership?” I was like, “Oh God.” It was such a burning tough piece of feedback, but he went on to tell me, “You’re the boss, be the boss,” and it was such a critical moment in my development as a CEO.

HOFFMAN: There are two things to love in this story from Jack. First, the way he described the “burning, tough piece of feedback” from Saar. Because it can actually feel like unsparing advice is boring its way into your soul! 

The other detail I love is how, actually, Saar’s advice was to not take the board’s advice so passively. Rather, his message to Jack was, If you want to be a leader, go lead! 

And that’s actually the best way to navigate difficult feedback. If it’s advice you know is right, take it with humility and thanks. If you’re not sure it’s right, ask another trusted advisor for a second opinion. And if you’re pretty sure it’s wrong, you can actually just ignore it. (Politely.) It will make you a better leader, and help you build your theory of the case. 

Rejecting advice forces you to articulate why you’re right, and your trusted source is wrong, just as Alexa did on the stage of Techcrunch 50. Did you notice the detail she shared about what happened next?

von TOBEL: I kind of just went into all of the work I had already done and ended up getting a standing ovation.

HOFFMAN: The judges didn’t see LearnVest’s potential, but the audience did. And when LearnVest officially launched less than four months later, in January 2010, the site got 50,000 signups in the first month. 

von TOBEL: That was when I was like, “There is something here, people do want to learn about this.” And then we raised lots of money, then life got easier.


HOFFMAN: And we’re back with Alexa von Tobel of LearnVest and Inspired Capital, on when — and when not — to take advice. If you’re enjoying this episode, advise your friends to listen too. Just tap the Share button on your podcast app. And to hear my complete interview with Alexa, including lightning round questions, become a Masters of Scale member at Or, you can join through the Masters of Scale Courses app, found in the app store of your choice. There are so many moments we didn’t have time for in this episode, like Alexa’s love of long-form personality tests. And, you’ll hear what she learned from her time at Dan Gilbert’s Happiness Lab. You won’t want to miss it.

Before the break, Alexa told us what it was like to launch her financial advice platform LearnVest, just a year after the world plunged into global recession. In fact, one of her biggest learnings was that the product she’d built for young people had a much larger total addressable market. 

How Alexa von Tobel scaled LearnVest

von TOBEL: What blew me away early was that 22-year-olds and 70-year-olds were buying, all over the country. Big cities, third tier cities. People with no kids, people solo. All shapes and sizes. And I was like, “Wow, this isn’t a young product. This is actually a mass American product. This is TurboTax for financial planning.” 

HOFFMAN: In building LearnVest, Alexa and her team harnessed the power of great advice plus a great delivery system. And to make sure the advice they were giving was unbiased, they built their revenue model on subscription packages — not on advertising specific products. 

von TOBEL: I was like, “We’re going to have a subscription service. It’s about $500 a year. You get to talk to an advisor one time, and then you get email.” All of a sudden, we realized companies would buy this in bulk for their employees. And so that’s when I was like, “This is a really big business.”

HOFFMAN: LearnVest grew steadily over five years, cultivating an audience of about 1.5 million users, and raising $75 million in capital. Alexa herself was named to many “30 under 30” lists of powerful women entrepreneurs.

von TOBEL: We had just been the cover of Forbes, as the millennial wallet, and this tsunami of people really starting to recognize that this fintech thing is happening online, and it’s real. 

HOFFMAN: Then one day in late 2014, Alexa got word from her head of business development. His name’s Kareem. He’d been receiving some emails from a major insurance company. 

von TOBEL: Kareem kept saying, “They really want to partner with us, and they want to figure out if they can give us some money.”

HOFFMAN: The insurance company in question was Northwestern Mutual. Founded in 1857, they were the opposite of a startup. But Alexa took the call. 

von TOBEL: We visited and we spent some time together, and they’re really sincere people, and they end up giving us about $30 million in our series D. And so, we started talking about how we could put together a partnership.

HOFFMAN: The ingredients of that partnership started coming together quickly — if not conveniently.

Northwestern Mutual’s acquisition of LearnVest

von TOBEL: The day before Thanksgiving, 2014, the CEO emailed me and said, “Hey, I’d love to come see you.” I had just gotten married, so I was actually hosting my in-laws. I love to cook, I don’t think I’m the best cook, but I was hosting, and I had this whole plan to be a wonderful daughter-in-law. And he’s like, “Can you be free? Five hours? Can we do five hours on the day before Thanksgiving?” And I was like, “Of course. I’m totally free.”

HOFFMAN: This is a quintessentially entrepreneurial reaction, and a great example of advice that makes sense in one context, but not another. Taking a five-hour meeting before a massive holiday gathering is generally a bad idea unless it’s to seize a unique window of opportunity.

von TOBEL: He came into our office. He was like, “Alexa, your value system is you believe that every American family should have access to good advice and transparent advice.” You know, “Northwestern Mutual is 165 years old,” and there was this beautiful story of their founding, and the fact that they have half a trillion dollars of capital, and do about $40 billion of revenue. He said, “What if we came together, and we combined our companies, and took your software and literally brought it to our whole company?”

HOFFMAN: Notice the part of the pitch that Northwestern Mutual leaned into.

von TOBEL: “You believe that every American family should have access to good advice and transparent advice.”

HOFFMAN: Alexa and her team had built a trustworthy brand that made them attractive to the insurance giant, and it stemmed from their mission to offer objective advice that wasn’t tied to any product.

It wasn’t the only acquisition offer LearnVest fielded that fall. But it stuck with her — not just because of the five-hour conversation right before Thanksgiving. There was also a personal reason Alexa felt drawn to the deal.

von TOBEL: I actually sent a video that said, “I haven’t told anybody why I’m doing this.” And the reason is: a Northwestern Mutual life insurance policy actually stabilized my family.

HOFFMAN: That’s right. Before his passing, Alexa’s father had bought a life insurance policy with the company she’d now be joining. 

von TOBEL: I just remember thinking, “I think this is the right thing to do with this product that I built, is to go give it so that more people can better understand how to manage through an acute risk, which is what financial planning is really all about.”

HOFFMAN: United around their mission of providing financial advice to everyday customers, Alexa didn’t exit after the $375 million deal. In fact, she stayed on as Chief Digital Officer, helping integrate the LearnVest platform into the insurance company’s infrastructure.

But Alexa did start a new side project that would soon lead her in a new direction. 

You may remember that when she was first building LearnVest, Alexa lamented the lack of angel funds in New York City. 

Long commutes to visit Bay Area investors brought home this coastal disparity. 

von TOBEL: I felt the gap so clearly after getting on six planes to SF and just being like, “This is New York goddamn City. This is New York goddamn City! We’re the capital of the planet in so many ways and a pioneer of so many parts of culture, food, finance, medicine, media, art, culture, food, all of these beautiful things. Why is there not more innovation here?”

How Alexa von Tobel founded Inspired Capital

HOFFMAN: Six years later, the investor landscape in New York hadn’t much changed. But Alexa did have new access to personal capital and a calling to do something about it. 

von TOBEL: I’d finished my third year at Northwestern Mutual. They had just offered to make me Chief Innovation Officer. And nights and weekends my husband and I had a little angel fund, where we had backed some really great companies, the likes of Lemonade, and Airtable, and Form Energy, and a bunch of other really great all generalist categories.

HOFFMAN: As an angel investor, Alexa was advising new founders the way she’d previously asked others to advise her.

And just like in the early days of LearnVest, this new “nights and weekends” project became an all-consuming passion. It was her husband who gave her the next piece of career-altering advice.

von TOBEL: My husband was like, “You would do this for free, you should do it for a living. You’re so happy.” He just looked at me and was like, “It’s time.” 

HOFFMAN: Our friends and family don’t always have the exact right advice for us. But when they do, it usually resonates in a deep way. 

Alexa left Northwestern Mutual, and started a New York-based venture fund, Inspired Capital. To kick it off, she sought out more advice from a trusted friend. 

von TOBEL: Penny Pritzker, who had been my mentor when you and I met her in the PAGE program.

HOFFMAN: That would be the Presidential Ambassadors for Global Entrepreneurship, under the Obama administration, which is where Alexa and I first met. Penny Pritzker was Commerce Secretary at the time, and a public servant deeply committed to empowering people through business.

von TOBEL: Penny and I became really good friends, and we have a lot of shared history. And I called, we were chatting, and I was like, “Penny, here’s my plan. Here’s the rough draft. Here’s what I’m thinking.” And by the end of it she was like, “Can I build it with you? Can we do this together?”

HOFFMAN: This isn’t always the outcome when you ask a mentor for advice. But when you solicit feedback from people you trust, unexpected partnerships can emerge. 

This even happened to me recently, when a fellow partner at Greylock, Mustafa Suleyman, contacted me for advice on a new AI company he was building. Our conversations went so well, I became a co-founder of Inflection.AI along with him! 

That’s how Alexa and Penny launched Inspired Capital in 2018, along with two other longtime friends: Lucy Deland of Paperless Post, and Mark Batsiyan of Northwestern Mutual. Their first $200 million fund was announced in 2019, and they closed a second $281 million fund in late 2021. 

The importance of trust

von TOBEL: What I’ve learned in my, now, almost four decades on this planet is that trust is the most important thing, period. End of sentence. And you need friends that you have perfect trust with and mentors and people where their intentions for you are pure and vice versa. Who go out of their way to help you figure things out. And it is the difference of a few of those moments that come together that create magic and that help big things happen.

HOFFMAN: This is exactly right. Even after all the learnings we’ve discussed on this episode, it can be hard to know when to follow advice, and when to ignore it. You must weigh who’s speaking, why they’re speaking, whether they have good motives, or good information. And get a few contrasting opinions just to be sure.

But if you start from a place of trust, even the advice not taken can help you get to scale.

On that note, we’ll leave you with a lightning round of some of the best advice we’ve gathered recently from our guests in making Masters of Scale.

Here’s Cindy Mi, founder of the online learning platform VIPKid.

CINDY MI: The best advice is from my MBA program, Vice Dean. He’s also my mentor. I wrote an essay about my past 12-year experience of brick and mortar company. And then my question to him is, “I can’t solve this problem. What can I do? What can I do?” And then he said “Slash and burn, and start anew. What are you afraid of? Just go for the dream.”

HOFFMAN: Next, a trio of founders who found inspiration from their parents: Padma Warrior of Fable.

PADMA WARRIOR: My dad when I went to IIT. He told me, “Eyes on the stars, feet on the ground.”

HOFFMAN: Saeju Jeong of NOOM.

SAEJU JEONG: Don’t be hard on yourself. It is a-alright, it’s okay.  

ADAM SKUSE: Who told you that?

JEONG: My life mentors and my mom.

HOFFMAN: And Linda Yates of Mach49.

LINDA YATES: My parents were very much entrepreneurs and said, “Don’t go into politics.”

HOFFMAN: And last but not least, a story from Phaedra Ellis-Lamkins. Before she co-founded the govtech platform Promise, she spent a short but memorable time managing the one and only Prince during a moment of transition.

PHAEDRA ELLIS-LAMKINS: Best advice I’ve ever received came from Prince Rogers Nelson. I called him one day, and I was stressed because someone had said, “I’m not coming to Paisley Park if Phaedra’s there.” He had had some financial issues from the team that was before. And so my job was to clean some stuff up, and everyone hated me like, God. Just imagine being the person that’s like, “So you thought it was a gift, you’re getting a 1099.” 

And so I called him, and I just was like, “I just want to be nice, and can you just tell them it’s not me, because he would often be like, ‘Phaedra wants me to do it.’ And I’d just be like, ‘What? You told me, this is what you want me to do.’”

And he said to me, “Phaedra, you just have to make a decision. Do you want to play in Madison Square Garden, or do you want to play in your backyard? I believe you are great enough to play in Madison Square Garden, but if you want to play in Madison Square Garden, you better get used to the sound of boos because the only place you won’t hear boos is in your backyard.” 

HOFFMAN: That’s advice anyone on a scale path can use, but you decide whether to take it.

I’m Reid Hoffman. Thank you for listening.

Masters of Scale’s mission is to democratize entrepreneurship. Launched in 2017 as a weekly podcast featuring Reid Hoffman, we’re now two weekly podcasts — Masters of Scale with Reid Hoffman, and Masters of Scale: Rapid Response, hosted by Bob Safian — as well as an award-winning daily learning app, a best-selling book, virtual and live events, and more, serving a global community of founders, funders, and leaders looking to innovate at scale.
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