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Three top tips on attracting investment and selling your vision

Jack has worked with growth-stage technology businesses his whole career and has been a partner to nearly twenty portfolio companies at PeakSpan Capital. He currently leads Payments, Supply Chain, and E-Commerce logistics. Prior to joining PeakSpan Capital, Jack worked for Stackpop, an early-stage startup where he helped build out a SaaS-based cost management platform to help CTOs and IT teams buy and manage their internet infrastructure.

Interview with Jack Freeman, Partner, PeakSpan Capital

It’s fitting that when DPW catches up with Jack Freeman, a partner at PeakSpan Capital, that he has the words ‘We Climb Together’ as his background.

He will, after all, be addressing the challenge of securing funding to take a startup to the next level when he speaks at DPW Amsterdam 2022 later this month. So, if you’re looking to scale that mountain and are an entrepreneur or founder looking to attract investment, then his presentation should be one you’re immediately marking in your diary.

To whet your appetite, DPW spoke to Freeman this summer to get his three top tips on attracting investment and selling your vision. First up, though, he gave us a sneak preview into what we can expect from him in Amsterdam.

“We will be looking at pitch-decks and discussing the 25-or-so slides you should be including in your pitch-deck to explain your positioning, your KPIs, your team, etc.” says Freeman.

We’re going to offer to review any entrepreneurs’’ pitch-deck and provide feedback, ahead of time, or after the fact. We’re also going to offer a Q&A opportunity to openly ask investors questions. So, founders can ask the kind of things that prospective investors are looking to see or find out what they view as potential red flags.”

It’s sure to be an enlightening look behind the venture capitalist curtain and is another demonstration of the kind of innovative thinking that DPW and companies like PeakSpan Capital are bringing to the conference.

In the weeks leading up to the event, though, startups might want to digest the three key principles that Freeman and other investment specialists want to clearly come across during any pitch for funding.   


We love hearing about the problem or pain point from a ‘boots on the ground perspective’ followed by the inspiration to solve that pain point through software.

Jack Freeman, Partner, PeakSpan Capital

Have a perspective

“One principle is to have a perspective,” says Freeman. “It’s most powerful when an entrepreneur can speak to his or her past experiences in the procurement world or vertical end market. We love hearing about the problem or pain point from a ‘boots on the ground perspective’ followed by the inspiration to solve that pain point through software.”

He goes on to say, “You need to have a thesis. The more that this thesis can be conveyed with thoughtfulness, conviction and authenticity – the more excited investors typically get. Demonstrating that past experiences have allowed the entrepreneur to develop a very informed perspective is very powerful.”

Why your startup?

“Secondly, they need to show why their company specifically is super-exciting and set up for success,” he says. “It’s one thing to have a thesis, an academic can have a thesis. The next step is to demonstrate dynamic such as having proprietary relationships, a superior business model, thoughtful revenue model and GTM approach what can clearly lead to high velocity.”

An investor will want to understand and appreciate the specifics surrounding how an entrepreneur plans to take his or her thesis and mold it into a growing, profit-generating business one day.”

Sealing the deal

“Lastly, it’s pulling back the aperture and saying i) here’s our thesis, ii) here’s our approach, and then iii) explaining why it matters and why it’s interesting in the context of this market. For example, citing the competitive field of battle and why your specific startup is positioned to win. Are you the “rolls Royce” of the market? Are you the cost-effective solution? Do you have a superior UI? Further, is the market so big as to support multiple winners and if so, who is your target customer profile and why are you best positioned to dominate that segment.

He goes on to say, “…more broadly, the company has to matter. It has to map to a broader vision of why this company NEEDS to exist given the immense pain currently being experienced across many companies and employees and where incumbents haven’t been equipped to solve the problem to date. Or perhaps there is a TON of value being left on the table and if not for this startup, that value will go to waste.”

“It’s three-pronged – i) what’s our thesis, ii) what’s our approach to make that thesis a reality and then iii) why it matters.”

If you can nail those three things, then investors will come running. But don’t take our word for it, come and hear it straight from the horse’s mouth when Freeman speaks at DPW Amsterdam 2022.   

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