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On today’s show, we are happy to welcome someone we’ve wanted to have on for some time now, Andrew Wilkinson. He is currently a Managing Partner at Tiny Capital, as well as the Founder of MetaLab, which helped design Slack. Along with this, Andrew is also invested in a range of other companies. In this episode, we learn more about his incredible journey and how he grew a passion for tech and design into a range of flourishing businesses. Andrew also sheds light on his investing education and overcoming his initial reluctance to see the power of investments. For Andrew, being an entrepreneur is about freedom to create the life you want, and having time to pursue your interests, which is how he saw the value of delegating. This is not easy when you are starting out your entrepreneurial journey, as Andrew knows, but as a company scales, so too should the owner’s levels of delegation. We take a look at the types of businesses Tiny Capital is interested in and why they are only pursuing simple business models. Our conversation then takes a turn into a different interest of Andrew’s — subscription podcasts. We discuss why these are such effective, yet untapped income-generating models and Andrew shares some of the work they are doing in this space. We then circle back to Tiny and leadership more generally where Andrew unpacks the importance of incentives along with his characteristic lazy leadership style. Andrew’s self-reflexivity and ability to talk openly about his weaknesses is truly refreshing. This conversation was a great look into what it really means to be an entrepreneur. Be sure to tune in today!
TIME-STAMPED SHOW NOTES:
[00:21] Before we jump into today’s interview, please rate, review, and subscribe to the Leveling Up Podcast!
[01:16] Hear more about Andrew’s background and his varied business journey so far.
[06:58] What led Andrew to learn about investing and what stood out to him in his education.
[09:39] Why Andrew is not a good CEO and what he has done to compensate for this.
[10:41] Learn about a launchpad business and the opportunities it provides owners.
[11:04] A common mistake entrepreneurs make: Building the first business to be venture-backed.
[12:50] What Andrew’s day-to-day looks like and the different activities he’s involved in.
[14:09] The kinds of businesses that Tiny Capital is currently interested in.
[16:05] How Tiny buys businesses and some of the terms they stipulate.
[17:01] Insights on how Tiny brings companies down from unrealistic venture valuations.
[18:05] Tiny’s organizational structure and tips for anyone looking to start something similar.
[20:58] Some of the characteristics that Andrew looks for when hiring a CEO.
[21:48] Why hiring great executives when starting out is so difficult.
[22:26] The different comp structures that are appropriate for these high-level executives.
[23:13] How Tiny interprets profitability and different ways to manage cashflow.
[24:18] The difficulties Tiny’s staff faced working on the range of entities and splitting attention.
[26:10] Find out about subscription podcasts and why Andrew is so passionate about them.
[31:09] Andrew’s interest in the No Code movement and why it’s valuable for business owners.
[35:02] The motivation behind Tiny’s Twitter ads and their efficacy in relation to deal flow.
[36:55] Andrew’s take on incentivization, common mistakes, and examples of good ones. [40:53] Incentive-related resources that have helped Andrew.
[41:47] How Tiny thinks about company culture after founders have departed.
[44:29] What it means to be a ‘lazy leader,’ and the role a CEO should play.
[46:28] Books that have shaped Andrew as an investor.
[48:11] Andrew’s favorite tool that’s not part of his portfolio.
Zack Onisko Shares the Trick to Getting Dribbble Millions of Visitors per Month with Zero Marketing
Zack Onisko Shares the Trick to Getting Dribbble Millions of Visitors per Month with Zero MarketingZack Onisko Shares the Trick to Getting Dribbble Millions of Visitors per Month with Zero Marketing
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Hey everyone, today I share the mic with Zack Onisko, CEO of Dribbble, an online community for web designers to share, receive support, and post/find jobs.
Tune in to hear Zack talk about some of the trends and constants that he’s seen around growth in the last 15 years, why he believes that the key to growth and success is focusing on developing a product so good that it can’t be ignored by the market and how Dribbble is killing it on a global scale with literally zero marketing efforts on their part. He’ll also share what Dribble has up its sleeve today.
01:06 – Led Growth at Hired.com and now is the CEO of Dribbble
01:24 – Who Zack is and what’s he’s up to
01:31 – He’s been been building high-growth startups for about 20 years in the recruitment and design space
01:45 – He’s a designer by training
01:50 – Moved into product management and growth for several companies
02:17 – Now CEO of Dribbble
02:41 – What are some trends and constants you’ve seen around growth at these awesome companies?
02:55 – Everything starts with a business model and audience—this defines not only growth strategy but business strategy
03:20 – It also comes down to product and market—how big is the market and how much can you sell your product for?
03:39 – Tell us about Dribbble and how to use it
03:55 – It’s a space for designers to show their work to other designers and receive feedback
04:03 – There’s a board for posting jobs which is, essentially, a community
04:20 – It’s a Top 1000 website in terms of rank and traffic
04:38 – They have millions of visitors a month
04:52 – Dribbble’s parallel would be Linkedin
05:02 – They have multiple business lines: ads, subscriptions, and job boards that each have their own products
05:17 – They’ve also acquired two companies: an iPhone app called Ballin’ and a designer developer marketplace called Crew
05:43 – What’s the vision behind the company, Dribbble?
05:52 – “We want to become the center of the universe for all things design” where designers can come for inspiration, training, and a community
06:23 – He also wants to be the place where people come to find work
07:36 – He wants designers to have seamless transition between contracts
07:47 – He also wants to help with legal help, contract negotiations, and accounting
08:22 – The job board, subscription and ads are split evenly in regards to what brings in their income
08:35 – What is the most effective thing you are doing for customer acquisition?
08:45 – They’ve done zero marketing
08:58 – It’s an invite-only community which has kept the quality of designers high
09:41 – They have community hosted meet-ups all over the world
10:46 – They only provide the swag (meet-up kit) and send it to the host, and the community takes care of the meet-ups themselves
11:21 – Direct traffic is their biggest channel as we’ve built this global brand
12:35 What are some trends you’ve seen around SEO?
12:49 – Zack takes a common sense approach making the site as easily as crawlable as possible; he looks at their inbound links strategy, and makes sure the content people are looking for lives on their domain
14:34 – As long as they’re producing high quality content, it’s going to pay off over time
15:53 – Dribbble has grown organically and leans on their rich content
16:41 – Zack discusses how they began purchasing other companies
16:50 – Zack and the team really wanted to build a mobile app
17:22 – He reached out to the top 3 IOS apps in the market and contacted the founders to join the team
18:24 – How do you decide which companies to purchase? – Dribbble’s parent company, Tiny Capital, which came from Metalab, has been very profitable over the years
19:10 – Their investment thesis: Instead of investing at seed level, they buy young companies that are profitable
19:18 – Andrew Wilkinson, from Metalab, is the Warren Buffet of Internet companies and Zack has followed his lead and worked together on the Crew acquisition
20:21 – There are advantages to having properties like Crew, like WeWorkRemotely, like Designer News, which are revenue-generating properties that do not take a lot of operating labour to keep them going
21:25 – Zack wouldn’t be where he’s at without being around amazing people
21:33 – Zack started at Tickle and worked with amazing talent such as Stan Chudnovsky and Michael Birch
23:10 – Coming from a design to product role, Zack went through a growth spurt learning how to build, test, and ship off a product
23:46 – Zack has learned that product design is what will actually impact growth the most
23:55 – What’s one new tool you’ve added that has added a lot of value to you? Zen Prospect – Zack used them for their hiring pipeline
25:21 – What’s one must-read book you recommend? – The Hard Things About Hard Things and Remote
26:08 – Contact Zack at on Twitter, on his blog or by email
26:28 – End of today’s episode
3 Key Points:
Everything begins with a business model and audience—this not only decides your growth strategy, but your entire business strategy.
Your product design and the quality you provide is what will impact your growth the most.
If you’re producing high quality content, this will drive your success and people WILL notice you.
Along with this, Andrew is also invested in a range of other companies. In this episode, we learn more about his incredible journey and how he grew a passion for tech and design into a range of flourishing businesses. Andrew also sheds light on his investing education and overcoming his initial reluctance to see the power of investments. For Andrew, being an entrepreneur is about freedom to create the life you want, and having time to pursue your interests, which is how he saw the value of delegating. This is not easy when you are starting out your entrepreneurial journey, as Andrew knows, but as a company scales, so too should the owner’s levels of delegation. We take a look at the types of businesses Tiny Capital is interested in and why they are only pursuing simple business models. Our conversation then takes a turn into a different interest of Andrew’s — subscription podcasts. We discuss why these are such effective, yet untapped income-generating models and Andrew shares some of the work they are doing in this space. We then circle back to Tiny and leadership more generally where Andrew unpacks the importance of incentives along with his characteristic lazy leadership style. Andrew’s self-reflexivity and ability to talk openly about his weaknesses is truly refreshing. This conversation was a great look into what it really means to be an entrepreneur. Be sure to tune in today!
