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Female Founders: Anna Ivey of Inline On The Five Things You Need To Thrive and Succeed as a Woman Founder

Building a product is different from building a business. I’ve been obsessed with our product from the beginning — these are college applications we’re talking about, so I wasn’t going to roll out something half-baked and then patch patch patch — but I’m also aware that despite the Field of Dreams, building it does not mean they will come. Sales and brand awareness are a whole different expertise and skill set.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Anna Ivey.

Anna Ivey is the founder of Inline, a digital tool that helps students with every question and essay on their Common App college applications. She is also the author of the book “How to Prepare a Standout College Application.” She lives in Los Angeles.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I’ve been in the higher ed world in some capacity for a long time now. I used to do admissions at the University of Chicago, I’ve worked in development at Stanford, and I’ve been running an independent admissions consulting firm staffed by former admissions officers for over a decade. I know how the proverbial sausage gets made, and I’m well aware that the path to higher education in the United States leaves a lot of people behind. And those who do manage to apply to a bachelor’s program often find that the admissions process feels like a giant black box. And that’s happening at a point in history when a college degree matters more than ever to succeed in the global economy for many kinds of jobs. So I’m on a mission to level the playing field on that path to higher education, and make sure that the best advice is available to everyone who is applying to college. And I also hope that by removing some of that friction and some of that mystery in the application process, more people feel encouraged to apply who otherwise wouldn’t.

Can you share the most interesting story that happened to you since you began leading your company?

I’m always learning about the hidden assumptions I sometimes make, especially when talking to counselors and applicants. Some of them are already very savvy about the application process, others are really starting from scratch. And I’ve learned never to assume too much in either direction. Years ago I was presenting at a conference, and afterwards someone came up to me — a young man who would be a returning learner, doing continuing education after some earlier credits in community college — and he told me that in my presentation he didn’t understand the difference between undergrad and grad school. That was an epiphany for me. I had assumed too much knowledge about higher ed lingo. And that learning curve never ends, by the way. Now I’m more likely to stop and ask people if I’m using terms they’re not familiar with. That’s the easiest and safest way to make sure they’re able to follow what you’re saying, and you don’t want them to feel embarrassed to ask, especially when frankly it’s my problem, not theirs. And I appreciate it when it goes in the other direction as well. In the same vein I had an admissions officer — from a fancypants college, one you’ve all heard of — ask me why she didn’t receive undergraduate applications from military officers. I’m glad she asked, because I realized she didn’t really understand some basic distinctions in military service, and that led to a much larger conversation about how to recruit more military applicants and how to interpret their backgrounds and service records.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I was doing a school visit and accidentally went to the wrong school. There were some signs that should have clued me in sooner than I realized my mistake. People were very nice about it though. You’d think by now I’d always know to go to this city’s airport and not that other one, or not to confuse two colleges that have the same name, or mix up two high schools. It happens. You’re not a robot. You fix your mistakes and move on. And you’ll never go to O’Hare again when you’re supposed to be at Midway.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My co-founder Alison Chisolm was instrumental in helping me build Inline. We go back many years. We worked together at the University of Chicago, we worked together in admissions consulting, we wrote a book on college applications together, and most recently we built Inline together. Our paths diverged over the years in between various jobs and projects, but it was wonderful to have a trusted partner to reconnect with all that time.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

I suspect the problem is less with founding than with funding. The statistics are even grimmer than the one you cited. Last year, only 2% of VC funding went to female-founded businesses. That should be a scandal.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

I’ve participated in two terrific start-up accelerators for underrepresented founders — one affiliated with USC and the other with Columbia — and they have been incredibly helpful. And let me also point out that they relied on a lot of free labor from the accelerator founders and the mentors they bring in as volunteers, all of whom take no cash or equity to keep the thing running. It is truly a labor of love on their part because they are trying to help fix some real inequities in the startup landscape.

That being said, you can have all the incubators and accelerators in the world to support female founders, and teach them all the things they could be doing better, faster, or whatever, but that’s also implicitly assuming that female founders are the source of the problem. I would ask investors to take a hard look at their funding patterns and ask themselves whether they could be doing better. Yes, female founders can always do things to make themselves better start-up founders and leaders, but I don’t think the entire problem should be laid at their feet. They are not the ones with the power or the checkbooks. The VC community tends to invest in people who look like them and talk like them and went to their small number of schools. And there’s that famous study in Harvard Business Review showing that VCs systematically talk about potential and opportunity when talking to male founders, but focus disproportionately on downside risk when talking to female founders. Can they be persuaded to shift their mindset? To invest more broadly? To diversify their investments (in multiple senses of the verb)? I hope so.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

I don’t think start-up life is for everyone, male or female or anything in between. But women have great ideas, and in some cases have very valuable vantage points, and we’d all be better off if they decided to solve some of those problems through business and private enterprise. I think women especially have a lot to offer when it comes to “product-founder” fit for their ideas. Some people end up in business school to pursue those goals, others learn by jumping in and doing. There is room for everyone.

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

A big one is that startup founders are young guys in hoodies. They do tend to look that way when you see who gets funded, but when you broaden the aperture to see who is actually founding and running businesses (with or without outside funding), that’s a whole lot of people who aren’t young guys in hoodies.

There’s also a myth around “hustle,” that you have to be psychotically dedicated to your business to the exclusion of everything else in life, but anyone who has a few years under their belt will confirm that that way of living is sustainable only in the short run. If you want to be doing something for the long haul, you have to keep learning and living and exploring outside your tiny niche.

A (considerably younger and junior) VC once told me on a phone call that if I’m not sleeping under my desk every night to run Inline, nobody will take me seriously. He also thought it was crazy that I had a day job. Well, my “day job” has been directly related to the expertise that supports Inline — we even use it with all our coaches and consulting clients — and allows us to be up to our elbows in the problems that Inline is solving. I also asked him how he proposed I bootstrap my venture in the absence of funding? He said to ask my parents to support me. Think about that. Aside from the class assumptions — a lot of founders or potential founders can’t just ask their parents for money, they don’t have a trust fund or a money tree in the backyard — I had to point out to him that I was in my forties and had been making my own living for some time. It’s funny, some funders want you to show that you have skin in the game — that’s a phrase I hear a lot — and when you actually have skin in the game, others will hold that against you. I’ve learned not to give any one piece of advice too much weight. You have to consider your sources.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

There are some people who are temperamentally better suited to work in a larger and more structured environment with chains of command and very clearly defined roles, and the upside to that (even for people who don’t like a strict org chart) is that you have a paycheck show up on a regular basis and probably someone above you to go to when you have a problem or a something you need help with. In contrast, as a founder you have to do everything, at least at the start, and you’re probably bootstrapping and investing your own funds, and that’s not an option for everyone. It’s also not something that everyone would find tolerable, let alone enjoyable. Some people aren’t comfortable with uncertainty or risk, and to them I would say: stick with your more conventional day job. There’s no shame in that. (There are risks with a conventional job too, of course, including unemployment risk!) To a founder, certainly in the early stages, you have to be crazy optimistic and resilient. You have to be committed to trading off a lot of other things you enjoy or want to spend money on, because most of the universe in one way or another is pointing towards not doing it.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  1. Building a product is different from building a business. I’ve been obsessed with our product from the beginning — these are college applications we’re talking about, so I wasn’t going to roll out something half-baked and then patch patch patch — but I’m also aware that despite the Field of Dreams, building it does not mean they will come. Sales and brand awareness are a whole different expertise and skill set.
  2. Be thoughtful about how much time you spend on pitch competitions. They can morph into a full-time job, and for many the payoff just isn’t there.
  3. You’ll go to enough start-up related conferences and events with male founders and you will observe a completely different baseline of confidence and entitlement, and some days I have to ask myself, “What would a white dude do?” It’s a different way of going through the world.
  4. VCs are a lot like admissions officers. They have big slush piles. You have to figure out what they want and how to stand out. They make a lot of assumptions about what you do and don’t know about their industry. You have to cast a wide net because to some degree it’s a numbers game. And they will often want you to do conflicting things in your applications/pitches. Then there’s the perceived black-box element around their decision making. Truly, I could write a book on the parallels.
  5. There are a lot of people who want to help you along the way. Sometimes you just have to remember to ask.

How have you used your success to make the world a better place?

One of the most rewarding things I’ve done, besides Inline, is to co-found a non-profit called Service to School, which mentors transitioning military veterans through the college application process and helps them get into good colleges. My co-founders and I were inspired to launch S2S because we were dismayed by the number of veterans being defrauded by for-profit diploma mills masquerading as universities. Since our founding over ten years ago, we’ve helped thousands of veterans pursue higher education. I’m not involved in day to day operations anymore — we’ve had a very capable, non-founder management team in place since we grew beyond start-up mode — but I still sit on the board. I’m really proud of what the S2S team has built and the good work they continue to do.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I’m far from the only person banging this drum, but the biggest obstacle standing in the path of higher education in the United States is a political one. We are one of the few countries in the developed world where higher education is not treated as a public good or publicly financed. When you see what hoops people have to jump through in the financial aid process, and the loans they have to take out, and the opportunities they don’t pursue because of cost, and the attrition rate that is often linked to cost, and you see how other countries have removed those obstacles, it really boggles the mind that we continue to finance higher education the way we do here in the United States. It reminds me in some ways of how we finance healthcare in the US versus the rest of the world. There really are better ways — honestly, they’re all around us — and we are mired politically in these broken systems. I have to believe we can do better.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I’m so inspired by Lynda Weinman, the founder of the online learning platform, which she built for years and eventually sold to LinkedIn. Talk about being in it for the long haul, and not looking like a young guy in a hoodie (love those cat eye glasses!) She’s had a vision and stick-with-it-ness that I admire, and she built something great. I think of her often! She’s originally from L.A., I believe, so whenever she comes back through town, please tell her that cocktails are on me!

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.



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Candice Georgiadis

Candice Georgiadis

Candice Georgiadis is an active mother of three as well as a designer, founder, social media expert, and philanthropist.