Scribbles from the Startup Frontlines: Lessons from my first rodeo
Startup investors need their first rodeo too.
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Today I thought we’d share a special treat with you all by sharing our resident Scribbler Serge van Dam’s latest columns out from behind the paywall to share with all subscribers.
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Scribbles from the Startup Frontlines: Wipster; My First Rodeo - By Serge van Dam
TLDR: Startup investors need their first rodeo too.
Putting up my Investor Socks
I was fortunate enough to have been in a successful exit. We sold M-Com early in 2011 with two-year handcuffs on our wrists.
By 2013, I was looking for new (ad)ventures to sink my teeth into. I ran into Sam Knowles in town (a total startup hero; founder of Kiwibank, then-chair of Xero, etc). He suggested I join the angel investment club he was part of - Angel HQ - and maybe look to get actively involved.
The first plausible investment we looked at was a company called Wipster. Its founder - Rollo Wenlock - believed that reviewing and approving videos should be like tracking changes in a Google Doc. As an active marketing leader who had made and commissioned many videos, I knew the pain he was solving for. And I liked Rollo’s energy, conviction and creativity.
Sam suggested that if I invested, I should also set up and lead the Board. I had no idea of or about what I was doing, but ever-the-pretender, I said YES. I have been a Director ever since. After 12 years as a Director of Wipster, I finally hung up my stirrups at the end of last month.
And it has been a journey for sure!
A First Time for Everything
I had been in one successful startup - and a couple of failed ones - before, but there is still a first time for so many elements of a typical startup, especially as a hands-on investor in a totally new business. Things I had never thought about, but all needed to happen in one way or another. Examples included:
Running / chairing an effective Board meeting
Evaluating and supporting and managing the performance of a CEO / Founder
Dealing with investors, including regular reporting to them (it felt like I was inventing SaaS metrics!)
Negotiating terms on an investment round, especially from institutional capital
Setting up an options schedule for the founding team and new employees, and convincing them to sacrifice salary in exchange for them
Building a self-service go-to-market model (I only knew how to sell stuff the old fashioned way; with sales people)
And so on…
There was a lot of ‘new’ there for me. But I never found it intimidating, even if I had little idea of what I was doing. I simply enjoyed the rate of learning, and the speed of both delivery and market feedback cycles.
Bumps, Grazes and Scar Tissue
But over the 12 years, we really have gone through all the highs and lows of a stereotypical startup journey. We have had our share of injuries and near-death experiences, often caused by our own poor judgments or mis-predictions.
We grew really fast early on. In a great way. We had invented a category and our timing was perfect; the world needed a way of reviewing and approving video. And we did so without much capital.
We soon partnered with Vimeo as our best possible market accelerant. But the deal was terrible (my / our fault) and they changed their mind (and their CEO) early in our relationship which was terribly costly to us, and our joint ambitions.
Our product was copied by some new kids on the block; Frame.io. They raised ten times the capital we had, and eventually got acquired by Adobe for USD $1.3 billion in an exorbitant deal (proportionally, they had grown less efficiently than we had, but as we learnt then, scale matters).
We moved some of the team to the US and set up an office there, but Covid made a misery of it, especially for Rollo and his family.
We have gone through a number of leadership and personnel changes; forced and otherwise. These are always hard, and don’t ever help customers much.
There are many more stories, but our core product and proposition remains indistinguishable. And the people who buy and LOVE the Wipster product are alike…. their feedback is still the same; “Wipster is the easiest video review and approval tool on the market”.
My Reflections
As you can imagine, I have many scars. But what did they teach me?
Below are some of the most impactful lessons of my last 12 years with Wipster.
The founding idea and purpose stick. The reason Rollo and the team established Wipster in 2013 remains core to why a customer will sign up in 2025. The WHY of a startup is like a tattoo. Think carefully on why the market wants you to exist.
It is hard to argue with capital. Wipster was largely beaten by a company that copied its core idea and product, but scaled much faster than we could have ever done. We did not have a response to that, and needed to. I will bet that it will happen to many readers of this column!
Startups make talented humans better. Many of the people who have been with Wipster as employees have gone onto bigger and better things. One of the Founders, James, is now in New York City as a Lead Designer for Shopify. Several other personnel have helped scale a different cohort of startups.
Startup is a contact sport (as I have said many times). It has been brutal in several ways; on the founders (personally and financially), loyal investors and some of the people who have lost their job on the back of one of our many changes. The punches to the face have always kept coming.
Whatever the outcomes, if you are working on a meaningful initiative, you will likely change the world for the better. As it was for Wipster, the core idea was always worth doing in the first place!
None of these are new to readers of my random startup scribbles. Wipster has merely cemented these deeper into my brain.
Everyone Needs a First Rodeo
Wipster will continue even after my ride is over (as a Director at least; I remain an investor and avid supporter, of course!). That’s what you always hope for; with your kids, the clubs you join, and importantly, startups.
Wipster has a great team, and thousands of users, even if we have not (yet) won our category. I hope the very best for the company as I let go.
I am very grateful for the opportunity to have been part of the journey. As a hands-on investor, I needed a first rodeo. And I sure got one.
Serge van Dam is an early stage startup investor, focused on going-global productivity software companies. He spends much of his time with a bayonet in hand yelling “now” in the startup trenches.
That’s it for today, thanks for reading. Want to get in touch with a news tip, bit of feedback or just to chat? Email hello@caffeinedaily.co