🤝 Catching up with NBA Player & Olympian Matthew "Delly" Dellavedova: Life Beyond Basketball as an Early-Stage Investor.

Who are the outside the box Syndicate GP’s and how do they think about allocating capital via SPV’s?

Start-up investor & Australian Matthew “Delly” Dellavedova is a 9 year NBA veteran, 2016 NBA Champion and 3x Olympian for the Boomers, Australian Men’s National Basketball Team. This season you can find him playing for the NBL’s Melbourne United.

Off the court Delly is passionate about investing and plans to make a full time career of it once he’s done playing professionally. Angel investing since 2017, he focuses on early stage start-ups and runs his own syndicate on the AngelList platform. He’s a strong advocate of Bitcoin, learning about and investing in it since 2020, and has recently joined Swan Bitcoin as Vice President of Business Development while continuing to play basketball. He is also a Partner at Athletic Ventures, a syndicate of current and former elite athletes that are investing in startups.

On a personal note, Delly likes a good book, coffee and avocado toast, working out, and spending time with his family.

Our interview with Mathew Dellavedova below:

1. Where are you right now and what are you doing (like work-wise)?

Playing professional basketball in Australia for Melbourne United this season. I just joined Swan Bitcoin as VP of Business Development in a role I can still do while playing which is really cool. I’m also a Partner at Athletic Ventures, a syndicate of current and former elite athletes that are investing in startups.

2. What got you interested in venture capital?

After signing in Milwaukee, my financial advisors wanted to allocate a % of my investment portfolio to venture capital. I didn’t know what that was or how it worked so I asked a lot of questions. They explained what it was and it sounded really interesting. Being an athlete is all about growing every day through adversity, these startup companies are attempting to do the same so I enjoy being on the journey with them.

3. Who were the most helpful folks in getting started in VC?

I’ve been very fortunate to have a lot of helpful people! The 2 main ones early on were - Jason Calacanis - read his book which provided a lot of practical advice then met with him and attended his Launch accelerator a few times which was cool. Nick Crocker from Blackbird in Australia, is an amazing connector- he opened many doors for me to build & grow my network and is a great resource to bounce ideas off of. 

There have been a lot of helpful people since then but the two who helped me syndicate my first two deals on AngelList were Bryan Rosenblatt and Peter Livingston.  

4. How have syndicates played a role in your path into venture (ideally you can allude to both investing in them and also running them)?

After I learned what Venture Capital was, I invested in some funds and a couple of deals directly. Then I found Angellist and started looking at a lot more deals. I think that really helped get a lot more reps and calibrate what’s a good deal. Once I got more comfortable, I had a goal of syndicating my own deal on Angellist once I found the right deal. When the NBA season paused due to Covid, I had more time and said I would try to syndicate a deal if the right one comes along. Luckily it did and I was fortunate to co-syndicate it twice and is currently sitting at an 11x and 7x multiple right now. At Athletic Ventures, I’ve also seen the power of athletes coming together as a syndicate to get a seat at the table of hard to access opportunities and also to support the founders in a differentiated way to the other funds.

5. How have you sourced deals? Based on your deal flow, it looks like you spend most of your time in the consumer space (e.g. Simple Lab, Underdog Fantasy, OrangePill, etc.)

From friends who are in Venture Capital or founders who I’ve invested in previously. I try to be as helpful where I can to founders and they often send me deals which is cool. I don’t have a specific vertical  - I’m open to looking at most things but have found myself most interested in Bitcoin and health companies recently, earlier the better.

6. What excites you most about an investment opportunity?

A lot of different things. What I can learn from the founder, is this going to make a positive impact in the world, size of opportunity, how early it is, do I think I’ll be able to help. Could be a combination of those things. 

7. Now that you’ve spent a few years in venture capital, what’s the biggest misconception that you’d like to share with new investors interested in the VC?

Rather than misconception, a few things I’ve learned or like to share with new investors:

• Set an allocation you want to put towards VC and spread it over 15+ companies, over at least a few years. VC is illiquid, not every company will be a winner unfortunately, macro events can impact valuations and funding availability

• Money isn’t real until it’s in your bank account, paper markups are great but companies can still go to zero

• Founders are doing their best so try to support them wherever you can - this is one investment for you, most of the time for founders this is their blood/sweat/tears for years with no guarantee of success, a lot of similarities to being an athlete. 

8. What has been the highlight of your NBA career?

Internationally, winning a Bronze Medal at the Tokyo Olympics in 2020 (2021) with Australia. In the NBA, Winning the 2016 Championship with Cleveland in the NBA. 

9. What is your most memorable VC moment or highlight of your time in VC?

Being very helpful to a company/ founders early on in their journey and having them introduce me as one of their most helpful investors in an intro. Having a couple of seed stage deals look like they’re on their way to being unicorns. 

10. Do you think more NBA players should be getting into venture capital?

Definitely! I think a lot is already but I think there is a lot of opportunity to get more into it. I’ve always mentioned it to teammates and said if there is a company you like or want to get involved with just send a DM on twitter. There is also an ability for these athletes whilst playing to support the companies they invest in and learn more about an industry, which then the potential help with their transition from sport into a job or industry they are passionate about.

11. Do you see a career in venture capital after basketball?

Yeah definitely! I’m really excited about my current role with Swan Bitcoin and I really enjoy investing in startups. I’d like to continue to grow my AngelList syndicate of investors (currently 442) and bring more deals to the table. As well as continue to help athletes access compelling opportunities via my role at Athletic Ventures.

12. Where can people invest with you?

I syndicate deals here https://angellist.com/s/matthew-dellavedova/HRjkr . I invest in a range of deals, mostly early stage. I have done 5 deals on my syndicate and co-syndicated a number of others. 

13. Do you want to team up to build an NBA alumni syndicate (exclusive to current and former NBA players)?

This is a great idea! There are already a lot of NBA players who are successful investors across a wide range of industries. I share deals and co-invest with a couple of different guys regularly so always open to doing that. I’m seeing more and more NBA names pop up on cap tables which is cool. It also seems like players are getting  into it earlier in their careers which is great!

In Australia, a mate Matt de Boer who played Australian Football is leading a syndicate for elite athletes in Australia called Athletic Ventures. He gets access to the best deals in Australia and also does a lot of cool educational stuff around startups for athletes. I can see this going to the States, so you might have to watch this space.

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✍️ Written by Zachary and Alex