For all the stats, theories and hypotheticals, it can be easy to miss the woods for the trees — to lose sight of the real, tangible challenge facing real women and real businesses; the challenges that can be measured in dollars and cents.

As common sense dictates, not every woman founder will have the same experiences, or face the same hurdles while raising venture capital, or afterwards.

We sat down with two founders who have secured VC funding, and who have unique stories to tell.

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Danielle Owen Whitford, Pioneera: “I would bootstrap as long as humanly possible”

Pioneera uses AI language analysis to help businesses prevent burnout among staff, and improve overall performance.

The business has been up and running for six years, since before AI was a buzzword. So far, the business has been funded through angel investment, and VC funding secured through accelerator programs, as well as grant funding from the federal government’s Boosting Female Founders Initiative and Accelerating Commercialisation grant program, both of which have since been discontinued. 

If she’d launched the business today, founder Danielle Owen Whitford says, she might have done things slightly differently.

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SPD: Why did you choose the sources of capital you did?

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DOW: My background is in corporate. I started the business because I wanted to prevent people from burning out like I had.

By chance, I met Nicola Hazell, who was director of SheStarts at the time, and she told me I was actually building a startup… even though I had no idea what that was.

I ended up going through the SheStarts program and another accelerator, and I learnt what startups do: create an MVP; get some customers; get some investment; and off you go.

Both accelerators had VCs as backers, so we got funding that way.

Later, when we needed another round, I went for angel investors because VCs were looking for much more stability, and for processes to be fully documented and working.

Angels, I found, wanted to back the founder as much as the business. They were people who knew me in some way, and who had some personal connection to the problem we’re trying to solve.

Most of my angel investors are ex-corporate or still in corporate; they have experienced burnout, or they know someone who has.

The grant funding felt like the right solution for us at the time. As a solo female founder, the Boosting Female Founders (BFF) Initiative came at the perfect time. We had raised half of our round easily, and the BFF allowed us to close it.

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SPD: If you’d launched today, would you do anything differently?

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DOW: In the last year or so, people have pretty openly been saying not every business is a good fit for VC. That wasn’t the case four or five years ago.

It felt like a production line, cookie-cutter approach, and you were kind of a failure if you couldn’t get VC funding.

If I had started now I would do things very differently. I would bootstrap as long as humanly possible. At the end of the day, what businesses need is money — you can get that from equity, debt or revenue.

In fact, I think you get a much stronger business if you have a mix of them all, and particularly if you can get revenue from the early days.

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SPD: Have you faced challenges raising capital that men in the same position might not have?

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DOW: I’ve known plenty of male founders who have an equally difficult time raising capital.

But in this day and age I think it’s ridiculous that we need separate funds and separate grant initiatives for women.

The money offered under the BFF, for example, was about 10% the value of other grant funding programs. I question the design of that program, and the process of having to raise matched funding when we know women receive only 4% of VC funds. It all makes it really prohibitive. 

You have to do the raise and the grant application in parallel, and both can take anywhere between a week and 18 months to be finalised. It’s a significant workload. 

Then, of course, you’ve got all the extra caring responsibilities, which typically fall to women — and I was a single mum through part of this, so I had no other option.

If the goal of these programs is to get women to participate in business and startups more, then it has to be easier.

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SPD: What would you like to see change in the funding landscape?

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DOW: I know a lot of VCs are talking about appropriate allocation of funds and inclusivity.

My question to them would be: How are you ensuring equity in every step of the process? 

In 20 years in corporate, I spent a lot of time balancing the scales and creating inclusive environments. 

For example, we were trying to increase the number of women appointed into senior roles, so we changed the process so that at every step we had one credible woman and one credible man involved — from the first screenings through to the final interview. Both had to be senior enough to stop the process. That’s how we created change.

The same applies to grants and VC funding.  You just need to get the right people driving it, with enough conviction, influence and persistence.

This is fixable. If you have the right process, you should get the right outcome. 

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SPD: What advice would you offer to women founders seeking capital and weighing up their options?

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DOW: I would be really clear on your options. VC is but one option. Angels are an option. Family offices, debt and bootstrapping are all options. 

We now offer specific programs for clients and we’re generating revenue that way — making money that we would otherwise have had to get from investors.

Some VCs don’t like you to dilute the focus on the technology, but I don’t think that’s right. I think you need to look at all options to keep the business going and to extend your runway as much as possible.

I would say to women in particular: If you’re super passionate about the problem you’re solving, hang in there. You don’t have to follow the cookie-cutter approach. There is not one way of doing things. You’re not a failure.

And don’t get too disheartened by all the negative figures. As a founder you have to protect your mental state and manage your energy, and that stuff can suck a lot of energy out of you. Know it’s there, but choose when you want to engage and when you don’t.

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Lauren Humphrey, The Mintable: “My expectations of what the business ‘should’ be clouded my ability to see what customers wanted”

One half of a two-woman co-founding team, Lauren raised $8.3 million for her leadership development business, The Mintable. In part, the money was intended to fuel a software product for managers, Tandem, which used AI and language processing to support employees in giving and receiving continuous, effective feedback. 

In May 2023, the founders paused their training product to focus on the tech. But, 18 months later, they made the call to discontinue the product and return to where they started.

Lauren doesn’t view this as a failure. There is capital in the bank, and The Mintable is running, “full steam ahead”. But she says the pressure she put on herself almost destroyed her — and the business.

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SPD: Can you talk me through the Tandem journey?

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LH: In May 2023, we were still running The Mintable training, but the market had dropped off a lot, and we were also building our software product, which was requiring more and more founder time. 

We decided to dedicate our focus 100% to the tech product, and that’s when we decided to create a sub-brand, to avoid confusion.

Tandem had a very small team, and within a year we conducted deep customer research, secured design partner customers, got the product into customers’ hands and started measuring engagement and improving onboarding.

We did everything ‘right’. We worked in a really scientific, hypothesis-based way, but ultimately the metrics weren’t adding up.

So, while it wasn’t an easy decision to shut down, it was very clear it was the right one. We played such a good game. We lost the game, but it was such a good game.

This is not a story about a failure.

I’m a female founder who has beaten the odds, raised money, pivoted twice, and was so responsible with my capital that I enabled a third pivot back into a training business that has value for other wonderful humans. That’s the story I want to tell.

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SPD: In hindsight, what went wrong?

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LH: Partly, we were a bit early. In an early version of product, we used a speech-to-text integration and our own large language models to process meeting notes and provide feedback to managers, which was unheard of at the time. Six months later, note-taking apps and Chat GPT were everywhere.

But the problem was not the tech.

There’s a disconnect between the buyer and end user. A manager who wants the product needs to convince HR and IT to add it to their systems .

Conversely, a HR team might buy and implement it, but struggle to influence whether managers use it or not.

You end up in a kind of love triangle between product, buyer and user. It’s a really hard market to make work. 

I also realise now that my expectations of what the business ‘should’ be were clouding my ability to see what our customers wanted.

While we were working on the software, people were emailing us asking for training. That’s what they wanted to pay us for.

I wanted to build software. But that was never what our customers were asking for.

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SPD: Having raised VC funding as a woman, did you feel extra pressure to succeed?

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LH: Definitely. The pressure I put on myself is almost what killed me. Discontinuing the Tandem product was almost the end of The Mintable, and my story as a founder.

I was leaning into this idea that I must build software, even though that wasn’t what customers were asking for, so I was trying to fit the mould of a ‘tech founder’, wearing the hoodie and hanging out with the engineers.

I felt a lot of imposter syndrome, and almost embarrassed about raising capital — I don’t know if that’s 100% a gender thing, but it’s a component of it.

So many women struggle to raise capital, so I felt I had to prove myself; to be a billion-dollar unicorn, right out of the gate.

It was like survivor’s guilt. Why have I raised this money and not others, when I know so many women who are so capable and so talented? I was constantly telling myself I couldn’t squander it, but that was so bad for decision-making and clarity.

I put so much pressure on myself to be someone else. And that was so silly, because what I love and what I’m good at, doesn’t fit that mould. And now I’m basically back at the beginning.

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SPD: How did it affect you, personally?

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LH: I do feel a little self-conscious about it still.

I don’t want to say I became a different person, because it was me and I own that. But I went from an abundance mindset to a scarcity mindset. I stopped celebrating the wins.

I was so afraid of failing that I started limiting my actions, which doesn’t do anything good for the people on your team, or your business or customers.

To be clear, at no point did any investor put this kind of pressure on me. It’s all internalised.

But I was working so hard to be this other type of leader, and we weren’t finding a market for the product. I wasn’t enjoying my days, and I was feeling really burnt out.

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SPD: How did your investors react to you discontinuing the product?

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LH: I feel extraordinarily lucky that my investors all had the grace to see what had happened, and to let me know it was OK.

I was ready to quit on myself, but they have convinced me I did not fail. They still believe in the problem, and they still believe I can solve it. In the absence of me believing in myself in that moment, they believed in me.

One of my investors told me discontinuing the product was ‘really strong decision-making’. I asked him: ‘Is that what this is? Because it feels like giving up.’

But if I look at it from outside of myself, that is actually what happened. I can see it now, but in the midst of it, I couldn’t.

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SPD: What’s next for you, and The Mintable?

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LH: I’m feeling optimistic. This is very much an in-progress story.

We’ve learnt that training, community and support for managers is actually what companies want and leaders need, and seeing that demand is very exciting.

I believe we can bring out the best in each other if we put our minds and skills to it. I have an opportunity to create a corner of the world where people can learn how to do that, and in turn, make their businesses more successful.

Personally, I’ve learnt to let go of expectations and to focus on being the kind of entrepreneur I want to be.