I’m Hugh, and my company is Switchboard. 

We've developed a product that makes integrating and connecting enterprise IT systems that power supply chains — like ERP, Warehouse Management, Transport Management, Inventory Management, and Auto Management Systems — fast and easy.

Coming from a supply chain, transport, and logistics background, I was the third employee at a previous startup in the same space.

During my time there, I constantly encountered the challenge of connecting various systems, which was complicated, costly, and time-consuming — even for a tech-savvy company like ours.

It was nearly impossible for our less technically sophisticated partners.

This inefficiency led to hiring 8-10 full-time employees just to manually process emails with PDFs, leading to added costs, delays, and inevitable errors.

Mistakes in supply chain operations can be extremely costly.

Switchboard's solution connects these systems more easily and quickly than the traditional, expensive IT consultant approach.

I previously helped grow a startup from seed to Series B, now valued in the hundreds of millions with multiple acquisitions.

Before that I worked at Uber in Australia and New Zealand, managing the driver app and the supply side.

My career began as a management consultant at BCG.

I’m well-versed in fundraising, having been deeply involved in raising funds for my previous business for the past five to six years.

I've raised 2 rounds for my own company and participated in 3 or 4 rounds for my previous one.

Fundraising is definitely becoming more challenging—processes are taking longer, valuations are lower, and VCs are more stringent in their requirements.

Due diligence (DD) has also become more rigorous.

When raising funds for my previous business, it took around 4 to 5 months per round.

The most recent round I closed took about 9 to 10 months, more than double the time. This was because of less capital in the venture space, and lead funds being more cautious with their investments, especially outside the U.S.

While U.S. funds remain active, European and Asia-Pacific funds have been more defensive, with some Asian funds just starting to deploy capital again.

This cautious approach has meant that I — and many founders I've spoken to — have had to engage with many more funds and face more rejections.

The DD processes, particularly for early-stage rounds, are much more detailed now than in the past.

Valuations have also decreased. When raising at Ofload in 2020-21, money was more accessible due to low-interest rates, resulting in high valuations.

That environment has changed; there is less cash available, requiring startups to be more cash-conscious and focused on strong unit economics.

Fundraising now requires starting much earlier. I’m already preparing for our Series A, knowing it could take up to a year to complete.

This stage is crucial for startups — a big milestone that requires careful planning and strategy.

We build and sell software, and my biggest expense is the team — people and salaries. I raised a pre-seed round in Q4 2022.

Before the seed round, our team was much smaller: just me, a head of engineering, one developer, a few interns, and eventually a mid-level manager, who we later let go.

It was a very lean operation. The seed round allowed us to significantly increase our headcount.

The most significant change was professionalizing our sales function. Hiring experienced Business Development Managers (BDMs) has been a game-changer, enabled by the fundraising.

We also brought on a product manager and more developers, improving our delivery speed and quality.

As we scale our sales team and see more volume, we need to execute effectively, which has driven our fundraising efforts.

The goal of our pre-seed to seed rounds was to build a solid MVP, gain initial customers, and show traction. Now, it’s about aggressively expanding our customer base.

While fundraising has fueled these changes, other factors also contribute, such as restructuring the sales team. More funding allows us to attract higher-level talent, and as a founder, tough decisions are part of the role.

It’s also important to recognize the value of just staying in the game for a few years. Our experience has grown, our product has become more robust, and we have a stronger team after thousands of calls.

Fundraising has led to substantial changes in team and capability, reflected in a tenfold increase in our pipeline.

But persistence is equally important. I raised $500k in pre-seed funding in 2022 and recently secured $1.5M in a seed round. I would have liked to raise an additional $500k, but current valuations don’t support that.

There's an extent to which the decision can get made for you, especially in this economy. 

If given the choice, you should make a very deliberate choice about who you partner with. 

But if you're talking to serious venture capital funds and you're circling around a similar deal with a few of them, it’s fine to take the money when you need to.

One guy that we ended up partnering with, the chairman of the fund is a billionaire who ran global logistics business Toll Group.

Coming from the supply chain world, that’s a great endorsement of the problem we're solving and the business that we're running. 

That investor also has a great rolodex for us to tap into. The other investor had good credentials in the space and had some good advisors that we liked.

But they also had some offshore presence that will help us in Asia specifically. 

We have customers in Australia and New Zealand, but also in the US, the UK, and the EU. 

The venture capitalists are going to give you money and they're going to give you intros. For early stage companies, that’s often the biggest value that you will get from them. 

If you're struggling with a big thorny issue, maybe they've got someone to talk to, but often they will be most useful for intros and connections to other people who will help you solve problems.

I would generally do cold outreach to VC funds. These days, it's more of a blend because we've had a couple of raises and a bit of media about it. 

I get a bit more inbound now, but I still do plenty of outbound too. 

A lot of cold emailing and LinkedIn outreach, but once you start talking to VC funds, they're all very willing to introduce you to other ones as well.

Especially when I'm fundraising, I will take every meeting because you just don't know. 

2 of the investors that joined in the last round, at the first call, I thought “it won't be these guys.”

I had well over 100 conversations with probably about 20-30 that got pretty interested. 

The short list was about 9 or 10, and then we got 3 checks.

This changed based on the stage.

For the upcoming round, we're going to emphasize very different things than we did at Seed. 

For Seed, we spoke a lot about the size of the market, the size of the problem, and our solution, because we had customers, revenue, and some data points.

In this upcoming raise we're going to talk a lot more about our customer base, our trajectory, and our forecasts.

We obviously had forecasts at Seed too, but not as extensive.

The other important piece of context to keep in mind is that I had to do quite a lot of education on these calls too. 

If you are at all in the supply chain world, what we do is front and center.

But most venture capitalists that deal with fintechs don't know a lot about supply chain and the systems or processes involved. 

I used to have to do quite a lot of education and that's normally at least its own call.

To be honest, this is not something I did well. This was a learning for me.

I didn't nail the timing, the power dynamic, and I didn't nail the urgency. 

Coming into the Series A, the world's very different for us now that we have a bunch of customers and a materially more developed business.

Based on the trajectories that we have, we should have more than enough traction to raise the round that we need to raise in the early new year.

I will be much more able to play the game and get that urgency and that FOMO on. 

I wouldn't describe myself as having done a particularly good job on that front last time, but there’s certainly value in recognizing that.

You can't have 100+ meetings and be told no 115 times and not have that have any impact on you.

It's taken me until pretty recently to come out of it, to be honest. It has a really big impact and it's really hard for it to not.

I'm a solo founder so I have to have these investor calls and then walk out of the room and still be a leader to my team. 

I still need to be upbeat, pushing them to do the right thing. 

There’s a balance of honesty around telling them that we want this process to be done, but it's taking a little longer than expected. 

Balancing that with telling them all that it’s going to be fine is tough.

It's an emotional tightrope to walk both internally and with your team. That was absolutely the hardest part.

I remember one investor, who actually ended up investing, said to me, “hang on a second." I was giving an example and he said, “I just don't believe it.”

He said that he knew someone who works in this business. He said he was going to talk to them. 

He came back a week later and said, “you were right. That's totally how it works. I had no idea that it was so manual.” 

This happened a fair bit where, we had to do supply chain 101, then we have quite a niche technical product, so we had to talk a lot about that as well.

For what we do, if you don't work in the industry, you probably wouldn't necessarily know or believe that there is as much manual handling going on in these major enterprise supply chains.

The general public might make the assumption that there's quite a lot more sophistication involved than there is in reality.

We also had to overcome a bit of doubt, but luckily, we did.

Start early, start often. The advice I was given was to never stop fundraising. Talk to lots of funds, talk to them as often as you like, as many times as you can.

You should be having these conversations, if for no other reason than to stay sharp. Fundraising is a muscle and you must get the reps.

I'm going to immediately contradict myself though and say, however, I have really valued taking a few months off fundraising. I finished and it was all a job done, just a few months ago.

I'm just now starting to get a bit more serious about it.

Having had a couple of months of breathing room, I've actually found it to be really valuable. 

It has been really good for me to recover and to really push my energy back into the team and really motivate and inspire the team.

And it's been high energy around here for the past couple of months, which has been great. 

My other piece of advice would be to understand that it is going to be hard and that you're going to face an enormous amount of rejection, that is 100% normal.

This is just the way that the game is played. As a founder once said to me, all you need to do is never give up. And while somewhat spartan and laconic, it's a little bit true.

It is a bit of a white knuckle grind but, it is totally doable.

One other point I would encourage people to think about is what sector in the market you're in, and if there are sector or industry-specific investors that are worth considering.

Lastly, you will have moments in your week or month where you have nothing to do, or have nothing very pressing to do, and you should not feel guilty about taking time out.

There is absolutely no way that the business isn't taking everything from you.

The one thing that you get is control over your time. You know you're going to work 80-100 hours a week, but you get to pick which 80-100. 

Don't feel guilty about going for a walk at 10:30 in the morning or if you've got a spare two hours, go and do whatever you want. 

Don't constrain yourself to this Monday to Friday, 9-5 thinking, because it's not accurate for your job.

If you’re an early stage company in Australia, I have found After Work Ventures to be really good. TEN13 has also been great. 

After Work Ventures in particular are really nice. There are young guys who get it, they're not founders themselves, but early stage is what they do and they get it.

Skalata in particular is very thoughtful. I never get replies to my update emails, which is not unusual, but they send me thoughtful responses and ask great questions.

There's a couple of books. Traction, by Gino Wickman should be required reading. 

There’s a great book about marketing. I read Trust Me, I'm Lying: Confessions of a Media Manipulator, it was also good. 

I also really like 537 Days of Winter. It's the memoir from the Australian Antarctic Expedition leader during Covid - they were stuck down there for 2 years and he went through lots of interesting leadership challenges. 

It's very insightful and interesting reading (but set within his anecdotes about Antarctica, makes it very engaging to read.

I personally enjoy listening to podcasts with the Australian founders.

But also, read some other stuff. Read a fiction book, listen to a podcast about something else.

I'm in an audiobook phase at the moment, but before that, for me it wasancient history.

I wasn't much of an ancient history person, but there's a podcast, which I really like. I'll go for a walk and listen to that.

Find ways to disconnect. It's really important to read some unrelated stuff too.

Remember that venture capitalists only care about fundraising. That's all they do. It's all they think about. It's all they care about. 

They will tell you about how they do all this operational help and that they know all these things, but their focus is very much on fundraising.

Just because a venture capital fund doesn't give you money doesn't really mean that you don’t have a good business.

Once you're dealing with venture capitalists, these people often haven't founded a business themselves.

When you're dealing with these venture capitalists, you must remember that many of the people you are dealing with are finance people.

Don't expect the world from these people. They might be able to introduce you to people who can, but that's kind of what it is.