Discover/Riding Unicorns/Matt Chandler, Principal @ Octopus Ventu...

VC admits venture industry isn't getting something right with founders

Riding Unicorns · Matt Chandler, Principal @ Octopus Ventures

“we're quite good at passing ourselves on the back of the venture industry, but, you know, there's always issues within any sector.”

28:20 / 28:53

Find this show

Find on SpotifyFind on Apple Podcasts

we're quite good at passing ourselves on the back of the venture industry, but, you know, there's always issues within any sector. And, yeah, I'd be really interested to understand what do you think the industry or most funds or most people within the space are maybe not getting right at the moment?

I'm gonna answer that in the framing of various founder groups that I've been speaking to recently, if that's alright, because, there you go. Classic. Think about our customer first. So what I've been hearing for the market in early stage

About this clip

Matt Chandler from Octopus Ventures acknowledges issues within the venture capital industry and begins to explain what VCs are getting wrong by focusing on feedback from various founder groups. He frames his critique around putting the customer (founders) first, suggesting VCs may be missing key insights about early-stage market dynamics.

Why this clip

A VC publicly admitting industry shortcomings and promising founder-focused insights creates tension that draws listeners in.

28:20 - 28:5333scontrarian take
vc-industry-critiquefounder-feedbackearly-stage-investing

Share

LinkedInX

What they said next

Why shifting from consumer to enterprise customers can destroy your startup

6:58 - 36s · founder story

More from this episode

Riding Unicorns

founder story

How chasing one big client almost killed 18 months of innovation

Matt Chandler discusses the dangerous trap of becoming too dependent on a large corporate client, effectively turning into their agency rather than building for the broader market. He explains how this client-pleasing approach cost his company a year and a half of valuable innovation time and caused them to lose focus on what the market actually needed.

6:23 - 7:0440s
client-dependencyproduct-market-fitcorporate-partnerships

Riding Unicorns

founder story

Why shifting from consumer to enterprise customers can destroy your startup

Matt Chandler explains how his company made a critical strategic error by pivoting from serving individual consumers to targeting enterprise customers. He breaks down how this shift fundamentally changed their product development approach and led them to waste development resources and finite capital by building in the wrong direction.

6:58 - 7:3436s
customer-segmentationproduct-developmentstrategic-pivots

Riding Unicorns

founder story

Why this VC's failed men's beauty startup taught him everything about timing

Matt Chandler from Octopus Ventures shares the story of his failed men's beauty services marketplace that launched in 2014, two years before the market was ready. He explains how they tried to create a male equivalent to Wahanda (now TreatWell) but had to shut down after two years of aggregating barbershops and other male grooming services.

3:16 - 3:5336s
marketplace-modelsbeauty-techstartup-failure

Riding Unicorns

market insight

VCs are too slow and entrepreneurs are questioning what value they actually add

Matt Chandler from Octopus Ventures discusses why fundraising takes 6-9 months and the core problems entrepreneurs have with VCs. He explains how capital concentration and FOMO leave many founders overlooked, while entrepreneurs increasingly question what actual value venture capitalists provide beyond money.

29:06 - 29:4439s
fundraising-processvc-value-addcapital-concentration

Similar clips from other shows

Venture Unlocked · Jack Altman

contrarian take

Most VCs won't give harsh feedback - here's why that's broken

Jack Altman argues that VCs avoid giving direct, harsh feedback to founders because it's easier to be a cheerleader and there are few incentives for brutal honesty. He emphasizes that building high-trust relationships between founders and board members is crucial to creating a safe space for difficult but necessary feedback.

10:37 - 11:0629s
board-dynamicsfounder-feedbackvc-relationships

Venture Unlocked

market insight

VCs discuss how $500B+ companies are changing early stage investing forever

A VC explores how massive company valuations (potentially $500B+ IPOs) are forcing early-stage investors to reconsider their approach to startup valuations. The discussion touches on balancing techno-optimist views with fundamental investing principles when early-stage valuations are 3-4x higher than historical norms.

27:50 - 28:2636s
startup-valuationsearly-stage-investingmarket-dynamics

The Full Ratchet

tactical advice

Some founders listen to burn rate warnings, others let their companies die

An investor discusses the harsh reality of managing company burn rates through market cycles. They explain how some founders heed early warnings about cash management and successfully pivot, while others ignore the advice and ultimately run out of money.

2:28 - 3:0941s
burn-rate-managementfounder-feedbackmarket-cycles

The Full Ratchet

personal lesson

Why missing power law winners should be your biggest wake up call

A VC explains how missing exceptional early-stage deals like Skype and Facebook at Insight Partners inspired the founding of 645 Ventures. He argues that in a power law world with limited massive winners, passing on exceptional companies should serve as a wake-up call for investors.

3:23 - 4:0239s
power-law-investingdeal-sourcingearly-stage-investing

From the blog

FrameworkOriginal Research

The 5 Clip Archetypes for VC Podcasts

10 min read

Want clips like this for your podcast?

We find your top 5-8 clips, write the hooks, and deliver ready-to-post content. First 2 episodes are free.

Get 2 Episodes Clipped Free