When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW
Anthony Bontrager and I are both recovering adtech founders. He’s a straight shooter, keen operator, and highly effective advisor to the founders he works with. But what’s most impressive about Anthony is his heart - I’ve seen his kindness and generosity firsthand over the years and have grown to respect him all the more. Lucky to call him a friend.
What made you decide to be a professional investor?
Having been an entrepreneur for a significant part of my career (20+ years), the path to becoming a full-time investor was both gradual and natural. Between startups I very often found myself helping other entrepreneurs or VC’s with introductions, diligence, networking, etc. purely as part of my being part of and giving back to the entrepreneurial community. I approached this both with the goal of helping colleagues but also as a learning experience. I really enjoyed the exposure to new ventures, ideas, teams, etc. and ultimately realized that investing in and helping other entrepreneurs succeed was where I’d find the most fulfillment.
What did you do before becoming an investor and how does that benefit your founders?
Prior to becoming a full-time investor, I was the founder/CEO of two startups and prior to that was a senior executive at two publicly traded companies in the telecom and broadcasting spaces.
What are your most successful investments so far?
As most investors would say, "I love all my children!” However, one company, Qorus Software, continues to raise the bar in terms of performance, transparency, and team cohesion. While we pride ourselves on the amount of diversity within our portfolio, Qorus again leads by example and is by far our most diverse team to date. Additionally, our investments in Usermind, PTO Exchange and Wicket Labs are exciting examples of founders grinding it out and driving growth.
Why should founders want you on their cap table?
I’m very much a roll-up your sleeves investor and am an active board member. This can take the form of working with founders to develop a more formalized go-to-market strategy, or a true financial/operating plan so they understand how their business operates and the KPIs necessary to drive to success. In other areas, it’s with critical customer or partner introductions through relationships I’ve built over nearly 30 years. Last but not least, is helping founders understand the necessity of proper governance - both at the board level but also at the operational level - and how this will provide long-term benefit for them. This is an often overlooked and least understood issue with founders and its critical to get this right at the start and build proper muscle memory for it.
How many new pitches (actual calls/zooms) do you take per month?
I take approximately 15 to 20 pitches a month. Any more and I feel you’re doing a disservice to the prospective companies and your existing portfolio commitments.
How many new investments do you make per year?
Our Fund has typically targeted roughly 3 to 5 new investments per year
What's your sweet spot(s) in terms of check size, valuation, and vertical?
For our technology investing thesis in the PNW region, our initial check size ranges between $500k to $5M, and typically look set aside upwards of $10M per company for follow-ons, etc. We invest typically at the inflection point of post-revenue/pre-scale, meaning we want to see some sort of modest traction with customers buying off rate-card, and not simply a collection of POC customers. Speaking of our technology investing thesis in the PNW specifically, our focus is on SaaS companies leveraging AI/ML across large datasets as the foundational element of their business. This can manifest itself across several verticals - productivity platforms, unstructured / structured data management, FinTech, sales enablement, digital media, etc. While we have some companies that sit a bit outside these areas, this represents the bulk of our focus.
What one portfolio company do you want to hype for us here?
Qorus Software. An exceptional team that’s taking significant market share in the sales enablement/RFP market and growing rapidly. Just crushing it.
What do you think the next ten years looks like for Seattle/Pacific Northwest startups?
The PNW region has always punched above its weight from an entrepreneurship perspective, but only recently has it gotten the respect it deserves from outside our region, thanks to the rise of unicorn companies such Concur, Auth0, Qumulo, Smartsheet, etc. I see this trend continuing as the region maintains its status as the cloud capital of the world.
What song is currently getting the most run on your Spotify/Apple Music?
Let It Ride by The Blue Stones
Favorite shoes?
To Boot New York brown monkstraps
Favorite cooking ingredient?
Wine
Anything else to say?
I love cycling in the Pacific Northwest, working with the best and brightest entrepreneurs our region has to offer, and am a proud parent of a CU Boulder student.