A Year in Review: 2022

As the year closes I’ve always found it cathartic to reflect on how I’ve done the last 12 months, what that needs work, what I appreciate, and what the next adventure might look like next year.

I share stories regarding: the formal launch of the Austin Venture Association and my experience as founding Executive Director, the formation of Austin Venture Fest as part of the Texas Venture Association, and ideas about whats next. All this organized into six major categories: experiences, resources, leadership, learnings, future, and some unexpected proud moments.

EXPERIENCES

In 2022 we saw the introduction and the first full year back in-person from the lifetime-defining COVID-19. Navigating the launch and directing a new organization in this time helped me hone in and learn new skills, specifically for planning large gatherings for an events-focused company like the Austin Venture Association.

Hotel Ella, the venue of the Venture Hotel event

I’m proud of the 3 big Austin Venture Association events I planned: the “Investor Reception” as a very popular first SXSW from pandemic, inside a Series C startup trendy office space, the “Venture Boat Cruise” eased us into the Texas summer as a nice double decker dinner & drinks experience on the downtown lake, and the “Venture Hotel” as a soiree at the historic and upscale Austin landmark— for a combined attendance of 650+ from curated guest lists.

My favorite experience was co-hosting Venture Hotel with the big deal / big personality, Peter Rex & his venture studio team at their impressively classy Hotel Ella. I also reached out to Ferrari as a brand partner, and it was fun to collaborate and dream up their presence with us for the evening. I thought to send a personal invitation to former mayor, senator, and as of Dec 2022 mayor-elect, Kirk Watson, who not only joined as our special guest but delivered a thoughtful message I know our venture community appreciated. I heard of many great new startup founder, venture capitalist, and LP connections that resulted in investments from that evening.

Outside my Austin Venture Association capacity, I launched the Austin Venture Fest. At varying levels, I supported, planned, and ran 20+ venture-related events inside of the first two weeks of October. This was pulled off with the help of 20+ exceptional cohosts, all willing to try something new with me.

The marquee event of the Austin Venture Fest was The Venture Crawl, which ended up becoming the largest gathering featuring Texas VCs in our state’s history. It was hosted simultaneously across 5 different downtown Austin locations, with 3 shuttle stops, attracting 1,300+ attendees. I attended Austin’s first Startup Crawl in 2011, and it’s been a long-time desire of mine to bring back the multi-location Crawl experience leveraging the downtown geography to feature new and existing VCs in the area.

Mass Challenge & Texas Venture Association’s “Investor Night” Mixer

In addition to all the planned events, it was a thrill providing the venture community the last minute exclusive chance to experience Tesla’s grand opening, “Cyber Rodeo”, at the largest factory in the world by volume. Throw in some extras: Post Malone concert floor tickets, Formula 1 VIP, Burning Man, what I un-charmingly refer to as the “triple-distilled” LP Networking private events, and more—  all were an unbelievable opportunity for Austin venture folks to even attend as they were hosted right “in our own backyard” at world-class venues.

RESOURCES

The Austin Venture Association launch announcement was well received, as I wanted to publicly position our story of the micro and macro conditions in the area while also inviting the community to see us as a new resource. Timing was tough on that because as I geared up to make a big announcement I realized we’d actually be on the same schedule as Tesla’s factory launch— literally the busiest news cycle Austin would have of the year! Everything went well though, resulting in 18 press hits & interview features within a 6 month window.

What I initially thought might be a quarterly newsletter ended up being requested monthly, with now 5 published editions, high open and engagement rates, and sent to a targeted reach of 6K+ people. Writing the newsletter was one of the most enjoyable parts of the job, as I loved to see and promote other organizations’ events and resources + I loved getting “RE:”s from the venture community. I’ve been asked to scale this out to cover venture-focused curated experiences and resources across the state.

Another fun (but in this case definitely meticulously detailed) resource was finally creating Austin’s first Venture Directory filled with 170+ organizations of what I call the “greater venture” community. This population is made up of not only VCs, but accelerators, incubators, studios, growth & private equity, etc. It helped me personally get better acquainted with “who’s all here” now, each firm’s thesis, news, and website. I’ve since directed traffic toward Austin Chamber of Commerce who keeps a now more updated list for the city. What started as maybe 15-20 venture firms that considered Austin has HQ or office here, grew to 70+ in less than two years.

It was an honor to interview one of those top new firms, the multi Midas Lister, billionaire venture capitalist, Jim Breyer of Breyer Capital. Uncertainty in the market started showing in the general news early 2022, so I asked if Jim might share first thoughts about how the startup and venture scene might play out in the city. Insights linked here.

Finally, I thought it was pretty good to have 53,000+ website visitors within our first year of launching— and with no marketing budget or marketing team! Our LinkedIn followers grew to 1,000 and Instagram followers to almost 300. (I actually think that part’s puny, but for a trade organization maybe not too shabby)

LEADERSHIP

Over the summer I had sent a quick note to Austin Chamber of Commerce’s Innovation Director, Roland Pena to see if Austin Venture Association should help them recognize local VCs and give away their “Investor of the Year” Award during their signature A-Lister event. Not only did he excitedly oblige, they generously acknowledged a second investor breaking out an “Angel Investor of the Year” award in the Investor category as well, blogged here. They became a real partner and advisory board member as well.

As Executive Director it was also my job to organize and add board memberships, which quickly jumped to 14 people on the total team of Executive + Advisory Boards. I’m proud that we not only met but exceeded our board / revenue goals for the year. I communicated about every other week via 20+ Board Briefings, which was also a lot of fun for me to review the weeks and fill in updates, ask for help, and otherwise keep our extended team engaged. The Exec Board and I also conducted monthly meetings via Zoom which I appreciated as straightforward and to-the-point as folks were mostly remote.

I loved working with leaders in my function in Austin and around the country. The National Venture Capital Association was great to work with not only as a new Executive Director, but to also swap stories with their group about what we’re observing and experiencing across the US. We ended up co-hosting a happy hour with NVCA while they were in town + we promoted a special price to the AVA network for their Board Member Excellence full day conference. Many VCs loved taking advantage of that great deal.

In the form of another last minute pitch, I came up with a SXSW Panel idea that we quickly pulled together over the summer. “Leading Texas’ Venture Networks: The New Wild West” is in the works to convene the heads of venture networks around Texas, and will be moderated by NVCA’s President & CEO, Bobby Franklin. More on that here.

LEARNINGS

Now for the things that aren’t as much fun to share, and not exactly proud moments.

I felt guilty about the major sacrifices I made with family, friendships, finances, and health. I’m a little embarrassed about the tradeoff I made, but it’s part of being a founder. I’ve learned how deep my commitment will go, but I would be more measured if I did it again.

There were a number of times I felt exhausted by some of the massive undertakings in level of work, new organization, and career milestones I took very seriously. For what it’s worth, I think I’ve properly identified most stressful challenges as “good challenges” and necessary parts of growth.

I was constantly considering and re-evaluating what the role of the Austin Venture Association’s cofounders and Executive Director required, and what qualities really anyone who’s looked to in a community should portray in a major time of shapeshifting. At the launch I felt that AVA needed a very different type of leader than when I left. In general I personally love exploring and learning the natural ebbs and flows of leadership & timing, as well as the concept of “wartime & peacetime CEO”.

I’ve also now found the best ways to operate at scale to be a single organizer and point-of-contact for a 1,300+ person record-breaking venture event for Venture Crawl. And also curate picky guest lists for small private LP gatherings. I’ve actually never really thrown an event before this year, and I’ve come to enjoy the time-crunch and high expectations during a few short hours of an event. Also managing two-way expectations of a large and diverse board with many different motivations was the best learning experience for me early-ish in my career.

This all made for quite a dynamic year. On one hand, I’ve had people wonder what the point of creating a venture association even was… and others tell me it was a genius idea to start a venture association and very much needed. There was scrutiny over our events being too exclusive, and in the same event, received feedback that it wasn’t actually exclusive enough.

I learned that one cannot make everyone happy, but we must do the very best we can with what information and resources we have. While every leader must be open to listen and understand feedback, they must also recognize and pay attention to signal versus noise to make the most appropriate decisions.

FUTURE

2022 meant a lot of duality. As an entrepreneur I learned not only to accept that but expect, and come to appreciate a future of dynamic and nuances.

Looking forward to a next 12 months full of more advancements, bigger and stronger ties, additional capacity, and continuing to build in new ways that continue to attract top-notch founders, investors, and ecosystem partners. Thanks to the many people who helped build this platform— I’m excited to scale.

It was a year of incredible growth for Austin and me personally, which means shedding old beliefs and environment to step into something new. One thing that’s never changed, is my mindset that if something doesn’t at least make me a little nervous, then I question why do it in the first place. Let’s do something big, challenging, and important.

Leaving this post on a high, I’ll share some highlights:

BONUS SURPRISES

  • Had a TV interview at Tesla’s party discussing their new impact in the region… while wearing a cowgirl hat at the factory, here.

  • Sold roughly $16,000 in Lucchesse Boots (someone please tell them to sponsor me haha)

  • Conducted 50+ coffee meetings at Codependent (they’re a downtown neighbor which made it easy)

  • Accepted an “Organization of the Year” award from the Austin Asian Chamber of Commerce at their 10 year anniversary gala recognizing work in the local Asian community.

CS Freeland Austin Asian Chamber Award
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Accepting an Award for Work w/ Austin Venture Association via Austin Asian Chamber of Commerce

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RECAP: iFly.VC Annual Conference 2022