Ep 16 – How to Succeed as a New Builder




Elizabeth MacBride is an entrepreneur, award-winning business journalist and an author with deep expertise in finance, technology and international business. She has been on the founding team of four startups, including Wealthfront, the first online financial advisor.

Her work has been supported by the Kauffman Foundation and Walton Family Foundation. During the pandemic, her stories from were used to reshape the federal government’s small business aid program and the U.S. Census Bureau’s small business reporting policies.

With venture capitalist Seth Levine, she is co-author of The New Builders. It argues that the future of the American economy depends on how well we understand the needs of the people most likely to launch businesses today – women and people of color. Launched May 4, it briefly topped books about Elon Musk and Jeff Bezos on Amazon.

In her journalism career, Elizabeth wrote or edited for Quartz, Forbes Magazine, Atlantic.com, Stanford GSB, CNBC, HBR.com, BBC Capital, Advertising Age, Newsweek and many others. Her stories have been viewed by millions of people worldwide and translated into languages including Arabic, Turkish and Armenian. 

She also has edited two books on retirement and Wall Street for Charley Ellis, board member of Vanguard Inc., and the author of the classic Winning the Loser’s Game. She is a single mother of two daughters and lives in Alexandria, Va.


How do you take your skills from a traditional career and transform them into the core of a monetizable business? How do you mine the experience, contacts and the tacit knowledge you’ve built up over years into value-adding assets Day One?

And how do you find creative and enterprising ways to take care of important parts of the business, but that you really hate or aren’t good at?

In this episode, journalist, author and media business founder Elizabeth MacBride, talks about how she leveraged her prior career, raised founder-fit funding, resourcefully navigated tough challenges and negotiations, and much more.

Episode Highlights

  1. How to use your previous career to jumpstart your entrepreneurial venture
  2. Things to consider before establishing a business path.
  3. How to set up the basic financial infrastructure you need for your business
  4. The importance of protecting your intellectual property
  5. How to find the right trusted professionals  for legal and financial well-being of your venture
  6. Why not to pursue venture funding especially for women over 30
  7. The simple and “safe” funding path to secure friends and family funding for small, fledgling ventures
  8. What makes a media business unique and challenging to run
  9. The only thing that matters for getting pricing right
  10. Ways to break into power networks for budding entrepreneurs.
  11. Intuition or planning? The correct way to lead a business, financially.
  12. The hidden risks of being too open with your business plans

Links and Resources

The New Builders – Elizabeth MacBride’s new book on the emerging early-stage entrepreneurial economy

Times of entrepreneurship :  Home of Elizabeth’s media business focused on early-stage entrepreneurship

Kauffman foundation: Leading foundation supporting entrepreneurs and entrepreneur advocacy in the US

New York Women in Business : Community for women entrepreneurs in New York, New Jersey and Connecticut

SCORE :  Nonprofit organization of volunteer business mentors for small businesses

SBA : US Small Business Adminsitration

Interview Transcript

Shubha Chakravarthy: Thank you very much for joining us today!  You are somebody who comes from both the view of an entrepreneur as well as an expert who studies entrepreneurs like yourself and me. I’m very delighted to have you.

Elizabeth MacBride: Thanks for having me. I’m happy to be here.

Shubha Chakravarthy: Starting off, can you give us a little bit of an overview of what the “Times of Entrepreneurship” is about?

Elizabeth MacBride: Yes. I’m a business journalist and I’ve been one for more than two decades. So, when I decided that entrepreneurship was one of the vehicles that I believed could really make change in the world I decided to launch a publication that would focus on this early-stage part of the economy.

Times of Entrepreneurship is a publication. People have gotten unfamiliar with the concept of journalism these days, but we do journalism that covers the early-stage economy. It’s a media business.

Shubha Chakravarthy: You have this long background in journalism. I remember reading some of your excellent pieces on Wealthfront and stuff like that, but what gave you the business idea for this platform?

Elizabeth MacBride: Well, it really started when I was talking to people some years ago about why there wasn’t more of a platform to write about the entrepreneurship movement and at the time I thought maybe I’ll just get a fellowship and figure out someone who would support me to do more freelance work. Eventually, I started to see it as a viable media business.

Journalism has really consolidated in the past couple of decades, which is a big problem, but about maybe in the past three or four years there have been some viable media businesses started and I thought that if there is one space that looks like it could be viable as a business and do important journalism, it’s early-stage entrepreneurship.

Shubha Chakravarthy: So, now you have this idea, you have the concept and you’ve seen it potentially work out as a business. What paths did you consider to bring it to life and how did you decide which path to take?

Elizabeth MacBride: I feel like that’s an ever-evolving decision-making process. I mean, for me, it really became possible because I pitched the idea to the Kauffman Foundation. That was way back in the spring of 2019. They liked the idea and they asked me to apply for sponsorship, it’s a for-profit company, but foundations these days have also been doing sponsorship to for-profit companies. So, that’s the avenue I took.

I needed a little bit of seed funding to get it off the ground and that was an $80,000 sponsorship from the Kauffman Foundation.

Shubha Chakravarthy: So, you have your grant or the sponsorship. What are the first steps you took? What did you tactically do next?

Elizabeth MacBride: This is not my first start-up. I’ve been involved in probably a total of maybe a half dozen — LLCs and other media businesses and a couple of hugely successful tech companies as well. I joined Wealthfront pretty early on in that company’s evolution.

This was the first one I had started, but one thing that I knew about myself was that if I didn’t get the kind of backend systems in place in a way that could really work, I’m talking about the accounting and filing the corporation paperwork, I wanted to get that in place in ways that I had to think about it very, very little as I was going forward. That’s what I worked on first, for the first month or so. I was getting that stuff in order.

Shubha Chakravarthy: Sounds like that turned out to be a good thing for you because it freed up your mind space to focus on.

Elizabeth MacBride: Exactly. I just think it’s really important, especially the accounting. I think some people do that well and naturally, but I don’t. So, I pay about $200 a month for a bookkeeping service called Bench. For me it’s well worth it because it just plugs in to my bank account and it is really easy.

Then my payroll service is Gusto. I made myself an employee of the company and that turned out to be a very wise move in retrospect because what happened to Times of Entrepreneurship, which has really been both a blessing and a curse, but I launched it and the second thing I did after I got everything in order is that I built a sort of a scratch website — a prototype website with a designer who is in Malaysia and I thought, “Well, $80,000 is not that much money, but let me just put something up, but it’ll help me get more sponsorships.” So, I put it up in mid-February of 2020, before the pandemic — right before the pandemic. If I had been launching a month later, I might not have launched.

I had this prototype website up and running and the pandemic hit and I thought, “Well, I know how to do journalism. There’s clearly a big need for reporting on this space right now.” All of the publications, if you think back to that time, were focused on health as they rightly should have been.

But some of the business impacts were not being covered in the ways that they should have been and so we jumped right into that and we did some really important coverage, including an op-ed piece in CNBC based on our work that the Senate used to reshape the PPP.

Shubha Chakravarthy: That must have felt pretty good.

Elizabeth MacBride: It did. As we’ve evolved over the past couple of years, we’ve turned into a small, but influential publication. We have ways to go to be profitable or as big as we need to be, but that was great in a lot of ways, although terrifying. Those early days of the pandemic were really scary.

Shubha Chakravarthy: So, we talked about funding and what you laid out just now was supremely helpful in clarifying the nitty gritty of it.

You talked about the seed funding from the Kauffman Foundation. Was there any other aspect of funding that you considered that you think would be instructive for people who are following in that path?

Elizabeth MacBride: Well, there’s a lot. I am very familiar with the world of venture capital from writing about it and have good friends who are venture capitalists. I’ve talked to probably a dozen venture capitalists. But at the moment, I am not actively pursuing that as a funding model. That could change.

One of my friends said to me, “What you take on when you take on investors is really expectations.” Again, this comes back to what I know about myself. I do not like other people deciding what I need to do. So, I’m not really pursuing that. I think there’s way too much pursuit of it.

I think especially women have such a small chance of landing the funding and the amount of time you have to spend working on that, I just think, why not get your business up and running.

But that’s my perspective on it and it comes definitely for women that are at least my age. I think it’s a little easier for women in their twenties to raise funding for VCs, but I did end up doing a very small friends and family round. So, that is I think, a worthwhile endeavor for people.

This was how the pandemic was somewhat of a blessing. There were lots of programs that enabled small businesses to draw grants and loans. My decision to put myself on the payroll and to be very formal about incorporating the company was key to that because I had all the paperwork I needed to get the loans and the grants.

Shubha Chakravarthy: I’m really glad you’re talking about that because in many cases it seems to be the most boring part and people tend to say, “Well, let’s not worry about that.” So, it’s great that you did it and it actually worked out for you.

You talked about a friends and family round of funding, which leads to the natural question because whenever we talk about investment, we are talking about value. How do you value a company? Leaving aside the question of specifics, how did you think about your business value as a concept?

Elizabeth MacBride: Well, so the friends and family round was really just a friend of mine during the pandemic saying, “Hey, I like the work you’re doing. I want to support it. How can I be a part of it?” So, I went to my venture capital friends and said, “What should I do?” They said, “Well, use a SAFE.”

A SAFE is sort of a vehicle for attaching a future value to something that really has no value and you can look it up online. It’s called “Safe” and it is a pretty simple document. You could just download it. You have to hire a lawyer to help you make sure that it fits who you are and who your business is, but it’s easy to find online. So, that’s what I used to base my friend’s investment in the company.

Shubha Chakravarthy: You mentioned a lawyer. So, did you actually go out and get a business lawyer? And if so, what worked for you?

Elizabeth MacBride: Yes, I did go and get an attorney. I got it through a friend of mine. A high school friend recommended a kind of general business attorney that he had used. He helped me a ton in the early days to sort of figure out both that Safe issue and to talk about the name and ownership issues for the company.

Shubha Chakravarthy: On that topic, did you take some legal steps to protect your intellectual property? Two things in particular — trademarks, times of fees and name and it has value and will have more value over time and obviously, your written outputs and any other media outputs. How did you think about protecting the business value of that?

Elizabeth MacBride: I didn’t probably think about it enough. I’ll be honest with you. Things happened so quickly in those days that two of the things I’m doing now are really thinking more consciously about the brand and it’s value.

I’m thinking more consciously about the website, which is also related. Remember I said that I put up a scratch website in the beginning. It still is the scratch website. The pandemic just happened and things were just up in the air and then I published a book. The past two years have gone by faster than I realized.

I also released a book called “The New Builders”. You can find it on Amazon.

Shubha Chakravarthy: Great book! I loved it.

So, this just triggered the question. It sounds like from a legal and financial angle, you recognize the importance of those and you also recognize that those would not be the best uses of your time or your talent.

So, the big takeaway for me was to find a good person you trust. Find them early and then trust them to do their job. Would that be a fair?

Elizabeth MacBride: I am a single mother and a writer and you have to know yourself to succeed most in most things and especially in being a business person, because it really is about maximizing your time.

Shubha Chakravarthy: So, now you have kind of the building blocks in place. What steps did you take to put the business on a solid footing while you were delivering on your mission, which is, to write about early stage entrepreneurship?

Elizabeth MacBride: That’s the part that I really feel like is a work in progress still because we have not yet come up with a successful business model for the company. I think there is one in reach and we’re close and we’ve had our first cash flow positive month.

Shubha Chakravarthy: Congratulations. That is huge!

Elizabeth MacBride: Thank you. It was good. We’ve really been sustained by foundation support but we do have clients. It’s just that we don’t have enough clients for our work to make us profitable and I don’t particularly like relying on these big sponsorships from the foundations.

I hope they continue and there’s no reason to think they won’t. But still, I’d like to have this more as an operating business. So, what we’re doing now is launching events where it’s a little bit easier to sell sponsorships.

Right now we’re doing what we call bespoke research, which is sort of like white papers and content for companies and then in addition, we are selling sponsorships of events, of the website, and the newsletter.

Shubha Chakravarthy: It sounds like it’s leveraging every aspect of your prior skills and background to generate cash flow that you can then use to buy yourself some runway to make this new venture an operating business.

Elizabeth MacBride: Yeah. I can tell you’re like a “business mind”.

I appreciate that. I could not have articulated that. but yes, that’s what I’m doing.

Shubha Chakravarthy: I’m trying to extract the lessons because it’s useful to me and I’m sure it’ll be useful to others as well.

That is a good segue. You talked about how you’re trying to establish revenue streams. These foundations as a revenue source is great, but it’s a bit lumpy and it’s a bit potentially unpredictable, right? You don’t have a right to go back and demand.

So, how do you then think about your customers, which could be the foundations, and your consumers, which could be entrepreneurs — people like me.

I don’t know if there are other groups of people that you’re targeting with your content. How do you think about these two different groups and keeping them both happy?

Elizabeth MacBride: Yes, it’s a challenge. People don’t recognize it necessarily but media businesses are like the original platform businesses. They’ve always had different groups of customers that they had to serve at one time.

So, how do I think about it? As I’ve learned to be a little bit more of a publisher versus the hands-on journalist, my attention is focused much more on the people who are responsible for our cash flow.

So, that is keeping the foundations happy. It’s making relationships with businesses who want to sponsor or want to reach the audience we’re building on Times of Entrepreneurship. So it’s those two key constituencies and then our investors.

The one or two that we do have for my friends and family round have become a bigger part of my time. I think of them as sort of my job and then I’m able to outsource and hire the work that I really love.

It does hurt a little bit because the work I really love is the hands-on journalism, but that’s work that can be done by other people. The work I have to do is the sales and the relationship management of the big clients.

Shubha Chakravarthy: It’s funny because I was interviewing a lady who’s a finance specialist. She’s now running a company that drives early cancer detection. She said that I had to fire the financial part of me and be the CEO. So, it sounds like you had to fire the operational journalist part of you and become more of the CEO to make sure that the business continues to be viable.

That may be a challenge, not just for you, but also for me and for virtually everybody who wants to try to become an entrepreneur because you get in because you love something and then you find that to be a successful business person you actually have to step away from that a bit. Is that consistent with your experience?

Elizabeth MacBride: Yes. I would say that. I think that’s been very true of my experience and it’s really hard because it is both what I love to do and also, I’m the name behind the company. So, when I do write a piece — and I try to set aside a day per week to write and I continue to write.

Every week I write a short introduction to my newsletter, so I’m still in the game and it’s still very impactful when I do that work. So, it’s just an ongoing challenge balancing that.

Shubha Chakravarthy: That’s one of my favorite parts, by the way. I love the introduction.

Elizabeth MacBride: Oh, thank you!

Shubha Chakravarthy: I open it just to make sure I don’t miss it. I love everything else, but I don’t want to miss the introduction. You can tell that you’re a journalist. It’s very clear.

So, we talked about how you have to keep these customers happy and both sets of constituent customers happy. Then as you think about revenue and pricing, what basis do you use to think about those and what principles or guideposts do you use to help make those decisions about pricing?

Elizabeth MacBride: It’s an interesting question because, I remember reporting years ago on a company that helped other companies figure out their pricing. I have a sales director who works with me on a commission basis and he’s been a great help in figuring out what the norms are.

There are definitely CPM rates attached to online media businesses but we’ve basically thrown those out the window. People that want to support Times of Entrepreneurship are really supporting journalism.

They are really supporting these concepts of diversity and entrepreneurship and impact in the early stage economy. Those ideas and getting associated with them are really what they’re supporting. So, pricing that is really just a question of what we think they’ll bear. So, that’s basically how we’ve been setting the prices so far.

Shubha Chakravarthy: I picked up two very interesting things, by the way.

Number one was clearly that you recognized and acquired professional help. For a salesperson, a big part of it is knowing what the market will bear. How did you find this person and how did you decide that they were the right person for your business, especially given this impact angle?

Elizabeth MacBride: So, I think this is a great strength that women entrepreneurs have, which is we’ve got these fantastic networks.

I found our sales director through a friend of mine. That’s just what happened and I looked around in the beginning and reached out to a couple of other sales people that I knew to see if they might have ideas.

But again, probably partly because of the pandemic he worked out because he was really good and also because he had the time in his schedule beyond his day job. So he works for us part-time.

Shubha Chakravarthy: So, it works out for him, it works out for you, and you don’t have to bear the full overhead of a full-time sales person.

Elizabeth MacBride: Right, exactly. So, it’s a good fit for now. As I hope we grow, there will be some other solution, but in terms of sales you can hire outside sales organizations. So, he could eventually be a director working with those people. There are other solutions for sales these days.

Shubha Chakravarthy: The way you became familiar with them was just kind of being around the block and knowing all the stuff you know about entrepreneurship, or how did you learn about all that?

Elizabeth MacBride: Well, this is an advantage of being a journalist. Whenever I have a question about something that’s going to require more than a Google search, I usually try and do a story about it. That’s how I generally learn about things.

I can’t remember if I actually wrote a story about sales but reaching out to people to say, “Hey, can I talk to you for 15 minutes about this?” is not a hard thing for me to do these days.

Shubha Chakravarthy: So, that’s why you have an inherent advantage of maybe over people who don’t have that.

Elizabeth MacBride: Right. But I think you can still ask, right? You can still say, “do you have 15 minutes where I can pick your brain about this?”

Shubha Chakravarthy: Which, naturally comes to the question of networks. You mentioned networks and I found that interesting because there’s two angles. Women are natural connectors for sure.

But on the other hand, there’s a lot of research that says that one thing that’s holding women entrepreneurs back is that they don’t have access to the right networks. The networks of people who have money, the venture capitalists, as you mentioned. It’s maybe the people who have the advice, the prior entrepreneurial experience, who can say, “Hey, don’t forget to hire a sales director”, or whatever the case may be.

What is your experience on the non-traditional side — the financial side of accessing networks. Have you been able to do that? What advice or learnings have you had for others who might want to break into those networks?

Elizabeth MacBride: I think this is really hard. I remember once I went to the Kennedy Center and saw Samantha Bee, she’s a late night comedian, and somebody in the audience said, “Hey, how can I do what you’re doing?”

And she got up and said, “Well, I did 15 years of low paid standup comedy for a hundred dollars a night before I got to where I am.”

I feel that is sort of my answer too in terms of networks. I mean, I started 20 years ago building up very rich networks as a journalist. You can’t just invent that wholesale. You have to work with what you have based on your career and your life path. My guess is just that what you have is richer than you realize — for women.

Shubha Chakravarthy: And how would you go about discovering the richness if you’re starting out?

Elizabeth MacBride: I think maybe as a basic step, if you’re a woman entrepreneur is really just sitting down and thinking about who you know. I don’t think women tend to look at relationships in terms of their richness and how they can leverage them.

So, maybe sitting down and just writing down, “Okay, these are the people I know. How could they help me in this?” It’s not that you’re going to ask them for a huge amount of work or money, unless it’s right to do that, but just to sit down and think about what you have in your network is a really good start.

Shubha Chakravarthy: Through your experience of writing “The New Builders”, are there other, I don’t want to say tip tips or tricks, but are there any other less obvious ways that non-traditional entrepreneurs can use to break into these power networks if they don’t have success through there?

Elizabeth MacBride: Well, the one we haven’t mentioned so far is an accelerator or an incubator, which the star of our book, Danaris Mazara, was able to do, right? She tapped into one called “Entrepreneurship for All”.

Yesterday, I spoke at an event with New York Women in Business, which is affiliated with SCORE, which is a network run by the SBA. So, there are vehicles and there are often community centers in your community that will have more access than you realize to angel investors.

For example, retired business executives really love to help up and coming entrepreneurs. They really love to do it. So, you just find the organization in your community and that’s another way you can tap into a different network.

Shubha Chakravarthy: Did you need to use them at all, given that you already have all of this?

Elizabeth MacBride: I haven’t so far, but I’ll tell you that yesterday I just submitted Times of Entrepreneurship for a pitch competition. So, what I have tapped into is not really an accelerator as a friend of mine runs the Miller Center at Berkeley.

So, she just threw Times of Entrepreneurship’s profile out to their mentor network and I got an ad-hoc mentor that way. and he’s been hugely helpful. So, he talks me through some hard stuff.

Shubha Chakravarthy: Switching gears slightly, we’re now coming back the finance track. That was a very rich vein to explore.

How do you think about finances and managing the finances of your business day to day? Do you delegate it completely? Do you keep one or two numbers in front of you? How do you look at that?

Elizabeth MacBride: I think I’m still learning that, honestly. I have this bookkeeper and there are monthly reports issued with that. I keep pretty close tabs on the bank account. I look at that every couple of days. I have a budget that I’m working from.

I think what I’m not great at yet, but what I’m working on is incorporating the knowledge of that budget into my day to day schemes so that I can understand how the cash flow in any given week is affecting our goals for the month.

For instance, today I’m thinking about bringing on a marketing firm. So I’ll probably, take a look at the budget today or tomorrow and say, “Okay, this is the amount that I know we are set to spend. If I add this much every month going forward, what does that do to our sales goals?” So, it’s adjusting in that way.

Shubha Chakravarthy: It sounds like you not only keep control of your budget, but you can even ask, is it worth the dollars? Because you can say, “I need to see X amount of sales for me to justify spending, $4000 or $5,000, whatever the case might be.”

Elizabeth MacBride: Right, exactly.

Shubha Chakravarthy: It sounds like it gives you a double benefit. Did you feel any internal qualms and did you have to get over the dread that a lot of people face when they think about finances? Did you face any of that? And if so, how do you overcome that when it comes to financial matters?

Elizabeth MacBride: I like money. Actually, I’m not super motivated by money, but I’ve always had a good time, getting things to work right.

To me, it’s sort of like a puzzle. So, I did not feel that dread. I’m not good at keeping track of the day to day expenses and writing all that down.

But what I do like is the aspect of finance where you’re piecing a puzzle together to say, “Okay, if our revenue is going to be X and our expenses are Y, how do we make that all work?” So, that’s kind of fun for me and there are so many tools to do it now so it’s not bad.

I think people have an emotional relationship with money sometimes that will keep them from using it and from seeing it as the tool it actually is. I don’t think I have that issue. So, that’s helpful.

Shubha Chakravarthy: I’m getting a sense that you use what you like, which is your strength and you edged your way into something versus doing what everybody says you should do, like the boring step by step situation.

Elizabeth MacBride: Is that right? I don’t know. I just do it the way it works for me.

Shubha Chakravarthy: Talking of financials and stuff like that did you ever do a business plan? How did you set the direction? Did you just go by instinct?

Elizabeth MacBride: Well, the Kauffman Foundation, in their sponsorship application was fairly detailed. So, that sufficed for a business plan.

Shubha Chakravarthy: And do you use that? Did you find yourself going back to that ever or was it kind of like, “I’m done because I got the money?”

Elizabeth MacBride: I think I probably would have, if the pandemic hadn’t hit. That upended everything. I had a plan and then when the pandemic happened I just thought, “What am I going to do?” And I thought, “Well, the first thing I need to do is conserve cash.” So, I think for the first three or four months, I wrote every single story on the site, which was beyond exhausting.

I don’t even remember exactly how I managed to do it. So that upended any kind of business plan. I was just reflecting on this today. I think now I’m at the point now where I’m like, “Okay, now I need to go back to the business plan or come up with a new business plan, which is one of the reasons that I put us in for this accelerator pitch competition yesterday, just because I think we need to get centered on how we’re going to grow.”

Shubha Chakravarthy: You’re almost reading my mind. So, what are your plans for growth?

Elizabeth MacBride: What are my plans for growth? Events, right? So, we are on a track to do, I hope three events in 2022.

The first one will be a virtual event for university entrepreneurship professionals and professors. We’ve lined up a great speaker, which is Stacey Vanek Smith, who wrote, “Machiavelli for Women.”

So, that’s one event and then there’s another that I have in mind for May. Then an in-person event centered around women and finance in September. Those are really the plans for growth for next year.

Shubha Chakravarthy: It feels like it’s a strategy that’s focused on getting a foundation set in the event-space and building off of your name in the content space and then exploring further expansions from that space?

Elizabeth MacBride: Yes, that’s right. I think one thing that women entrepreneurs have to keep in mind is that they shouldn’t talk too much about their plans for the future. I think women, more than men, are vulnerable to people stealing their ideas.

Shubha Chakravarthy: You think so?

Elizabeth MacBride: Yes, I do.

Shubha Chakravarthy: Why is that the case?

Elizabeth MacBride: I don’t know, but I’ve seen it happen a lot. So, I think it’s true.

Shubha Chakravarthy: I trust your instinct on this, given your experience, but I have never thought about that. It’s actually a good caution for me and I think for many more women because I think there’s a chance that you’ve come up with an entrepreneurial idea because there’s a problem that you see that hasn’t been solved in by itself. It has protectable aspects to it. Thank you for that.

Then talking about this aspect of women versus male entrepreneurs, I want to touch on a slightly different aspect, which is this part around negotiation and showing up with credibility with hard audiences, like bankers. How has your experience been? How would you rate yourself as a negotiator? How important is it and what has been most useful to you in encountering those or navigating those successfully?

Elizabeth MacBride: I think I would rate myself as poor on the negotiation side. I think it’s really hard for women and for me particularly. What I’m mostly try and do is get someone else to do it right. So, although that doesn’t always work, there is a woman in my network who’s really good at negotiating. It is my friend, Elaine and we pitch business together.

So, when we pitch work together, she handles most of the negotiation because she’s better at it than I am. She keeps a cooler head. Beyond that, I also rely on my sales director. I outsource it because I think it’s just not a natural gift that I have.

Shubha Chakravarthy: I’m wondering if you’re unconsciously making a calculation that paying them for a skill that they bring to the table is in the long run cheaper than trying to cut on that expense and losing out on the elephant?

Elizabeth MacBride: Yes. I’m probably unconsciously doing that. Again, it comes back to just knowing yourself, right? I know my strong points and my weak points and that’s a weak point. I try very hard these days to be reactive, more than proactive in financial situations.

Shubha Chakravarthy: That’s interesting. It’s the opposite of what I would’ve expected. Tell me more.

Elizabeth MacBride: This is a new realization that I’m having, but I think one of women’s problems in the world is that we don’t recognize our own value. People will see us as more valuable than we see ourselves.

Shubha Chakravarthy: Don’t anchor yourself too low is what I’m hearing, is that right?

Elizabeth MacBride: Yes. That is the economic concept there — don’t anchor yourself too low. I think women, in reaching out, automatically anchor themselves too low.

So, sometimes I just try and be reactive. I don’t have a clearer way to say it than that, but wait for people to come to me, to ask me to do things.

That’s automatically a better position and if I’m entering into a negotiation with someone trying to be slow about it, just waiting for them to make a move, I feel like I know what they’re thinking before I make a move.

Shubha Chakravarthy: It’s fascinating. I think that’s one of the gems that I’m definitely going to have to pull out and showcase a bit.

This has been a fascinating discussion on the negotiation aspects, but more broadly, if you step back and say, “Okay, I’m an entrepreneur and I’m a woman.”

How has being a woman shaped your entrepreneurial journey? What would you say is the impact? How did that shape your journey?

Elizabeth MacBride: I think the reason I’m an entrepreneur because I’m a single mother. The flexibility was hugely important to me as I was raising my two daughters. So, that is why I started my own company, essentially, along with the other reasons that we’ve talked about.

Then beyond that, of the reasons I’m interested in having Stacey speak at our event is that I really disagree with some of the things she said in “Machiavelli for Women”, about keeping silent about being a mother because I never did that and I think in many ways it actually helped my career.

It might have hurt it in ways I don’t recognize too, but I think mostly it helped it. So, it’s just very core to who I am. Balancing my work with my children has been a big part of that and entrepreneurship has enabled me to do it.

Shubha Chakravarthy: Would you feel comfortable talking about it, an example of how it helped you to be open that you are a mother?

Elizabeth MacBride: Well, so part of being a journalist and I think actually part of being a woman, raising money or establishing a business is being likable and relatable. So, I will often take my kids when they can miss school or when they don’t have school.

They’ve often accompanied me on reporting trips, which automatically creates some sympathy with whoever I’m with. So, there are some people, and I think the argument in “Machiavelli for Women”, is that you don’t want that kind of sympathy, but I’ve always found it helpful.

I think it depends probably on the kind of business you’re in. You don’t want to go into your doctor’s office and see their kids. You don’t want them to be multitasking but being a journalist and a publisher it has been easier.

Shubha Chakravarthy: What’s your vision? If all your wildest dreams came true for the Times of Entrepreneurship, which I hope they do, what will that world look like?

Elizabeth MacBride: I have said from the beginning that I want to create a competitor to the Wall Street Journal 50 years from now. We should be a publication that really has redefined business and on that looks at business in a different way.

Shubha Chakravarthy: And how would you characterize that different way?

Elizabeth MacBride: We look at the impact on individuals and communities, not just institutions and we care about more than profit.

Shubha Chakravarthy: So, it’s a triple bottom line view of journalism versus triple bottom line view of business. I love it. It’s fascinating. Any words of wisdom for other women who might want to start media businesses like you?

Elizabeth MacBride: Well, maybe don’t do it. I think media businesses are very hard. They are becoming more viable, but they’re still very hard.

Starting a business in general is a great thing to do though. So, my advice for starting a business in general is just to get the funding first and to have a little bit of funding first before you launch.

Shubha Chakravarthy: Do you have any mile posts or any kind of markers for how much is enough?

Elizabeth MacBride: For me, it’s always been three months of cash of operating expenses.

Shubha Chakravarthy: So, if you had payroll, rent, and such, then all of that included at least for three months before you move forward?

Elizabeth MacBride: Yes.

Shubha Chakravarthy: Then I’m going to ask one wrinkle on that question. You’re a new builder, I’m a new builder. We’re not the traditional, white, male, 20-year-old entrepreneurs.

Is there anything you’d add if you were a new builder or in particular a second career entrepreneur where you’ve already done some other stuff and now you’re coming into the entrepreneurship fold?

Elizabeth MacBride: I don’t know if there’s anything I’d add, but I think probably the advice that plays the most to people like us is that we have more riches than we know in our network because our networks are bigger, right?

Probably we’ve both forgotten a lot of people who could help us at this point in our career so spending some time thinking about that could be useful.

The other thing I would say is that you should just do it right. I have reflected a lot on the fact that it’s good to be an entrepreneur at this age because I do have some perspective on it. When I think about, “Oh, what if the business doesn’t work? What if I don’t meet my goals?” I have the perspective to know it’s not the end of the world.

My identity is not entirely wrapped up in the company — a big chunk of it is, but it’s not as if I were 35 and doing this.

Shubha Chakravarthy: That’s great advice. Thank you so much for joining us today!