The Startup Playbook Podcast

Insights and lessons from the world's best entrepreneurs and investors

Ep166 – Dan Krasnostein (Partner – Square Peg Capital) on teaching, culture and conviction

My guest for Ep166 of The Startup Playbook Podcast was Dan Krasnostein, Partner at Square Peg Capital.

Dan began his career in management consulting before making the switch to joining Seek in strategy roles.

After spending 4 formative years at Seek, Dan was ready for a change and despite in his own words not knowing too much about Venture Capital, ended up joining Paul Bassat and the team at Square Peg Capital as their first hire.

Fast forward 10 years and Square Peg is one of the leading Venture Funds in Australia with over $3B in funds under management and a stellar portfolio of companies including the likes of Canva, Airwallex, Fiverr and Stripe to name a few!

Square Peg is one of the few Australian VC funds with a global presence and focus, having investment teams based in Australia, Israel and SE Asia.

In this episode we dug into Dan and Square Peg’s investment approach, covering topics such as:

  • How Square Peg assess founding teams for cultural and team fit when making investment decisions
  • Their conviction based strategy approach (i.e. larger cheques into smaller deals)
  • Their approach to building companies over the long term
  • Dan’s common thread of teaching throughout his career
  • What founders can learn from global operators
  • The challenges and opportunities in the current global financial climate
  • & much more!


  • 3:57 – Dan’s background, journey into venture and why teaching is at the heart of Dan’s career
  • 11:08 – Dan’s lessons from Seek on the importance of people and culture within an organisation
  • 14:15 – Strategies for developing great culture
  • 17:30- How Square Peg assess the culture of a team before investing 
  • 21:25 – Good questions to ask potential employees or co-founders
  • 23:12 – The two extremes of how venture funds can operate, and where Square Peg sits on the spectrum
  • 30:58 – Different approaches for investing domestically vs internationally
  • 37:12 – Commonalities in the global startup community which Australian founders can learn from
  • 41:34 – Valuing long term growth over short term metrics 
  • 47:19 – The challenges and opportunities of the current economic climate

Our partners

A big thank you to James Tynan, Dan Adams and Tim Harley for their help with this interview. Also a big thank you to our partners for this episode.


Lawpath’s Legal Advice Plan gives you access to lawyers on demand for one low monthly fee. Create legal documents, sign online and have a lawyer on-call to help you through any legal need for a fraction of the cost.  Lawpath has helped Australian businesses save over $100 million in legal fees, and are offering Startup Playbook listeners up to 20% off their most popular legal plans. Visit for your exclusive discount and discover an easier way to get your legals sorted.


We’re Scendar, an accounting and advisory practice better described as Finance as a Service (FaaS). We’re focused on founders, funders and startups. Clients that are ever-changing and adapting. We like fast movers. And as you might have guessed, we’re not your basic accountancy. We can take care of tax and the books whilst building a syndicate fund and a multimillion dollar exit strategy.  At Scendar, we’re empowered by our client’s potential. Find out more at

Dovetail Studios 

Dovetail Studios operates a venture studio and VC to transform ambitious ideas into unstoppable businesses. On top of being a renowned product development partner for startups like Afterpay, they also operate a VC fund to invest in early-stage companies that go through their venture studio program. So if you’re a non-technical, early-stage founder looking for a talented team to help supercharge your success, check out

Links Mentioned:

Dan’s Links:

People mentioned:

Companies mentioned:

Feedback/connect/say hello:

[email protected]
@RohitBhargava7 (Twitter)
/rohbhargava (LinkedIn)
@rohit_bhargava (Instagram)
My Youtube Channel


Music: Paycheck

Other channels:

Don’t have iTunes? The podcast is also available on SpotifySoundcloud & Stitcher Audio Player.

Find all links to the podcast here.