20VC Hootsuite's Ryan Holmes on Optimising Productivity in Meetings, Creating An Ownership Culture & Lessons From Running A Pizzeria!

In this episode of "20 Minutes VC," host Harry Stebbings interviews Hootsuite founder and CEO Ryan Holmes, discussing his journey from high school entrepreneur to leading a globally recognized social relationship platform with over 15 million users. Holmes shares insights from his diverse entrepreneurial background, including the lessons learned from running a pizza restaurant and how it informed his approach to managing a large company. He emphasizes the importance of maintaining an entrepreneurial spirit within a growing business, fostering innovation through initiatives like Hootsuite's labs division, and the challenges of product development in a customer-driven social media landscape. Additionally, Holmes touches on fundraising strategies and the evolving landscape of venture capital, while also providing his bullish outlook on Snapchat's future.

• Ryan Holmes is the founder and CEO of Hootsuite, a leading social relationship platform.
• Hootsuite was started in 2008 and has grown to over 15 million users, including more than 800 Fortune 1000 companies.
• The company has raised over $250 million in venture funding from firms including Accel, Insight Venture Partners, and Fidelity.
• Ryan Holmes has a history of entrepreneurship, having started multiple ventures including a pizza restaurant and a digital media agency.
• He is also an angel investor with investments in companies like Gusto, Bench, and Immediately.

"Now, Ryan is the founder and CEO at Hootsuite, the company he started in 2008 and has helped to grow into one of the world's most widely used social relationship platforms, with 15 million plus users, including more than 800 of the Fortune 1000 companies."

This quote underlines Ryan Holmes's significant role in establishing and growing Hootsuite into a major social media management tool used by individuals and large corporations.

• Ryan began his entrepreneurial journey in high school with a paintball company.
• Post high school, he attended business school but dropped out to pursue hands-on business experiences.
• Holmes started a restaurant, which he later sold, and then founded a digital media agency in 2000.
• The agency developed various products, leading to the launch of Hootsuite in 2008 due to a market need.
• Hootsuite experienced viral growth and product-market fit, leading to its success.
• Initially bootstrapped within the agency, Hootsuite eventually sought financing to scale.

"I started my first business in high school. It was a paintball company... I went to b school and did a couple of years there and then I just got kind of impatient... I started a restaurant, did that for a couple of years... sold that business and started an agency in 2000... ultimately 2008 when we launched out Hootsuite."

The quote provides a brief overview of Ryan Holmes's entrepreneurial background, highlighting his early start in business, his impatience with formal education, and his hands-on approach to learning through starting and running businesses.

• Holmes learned full accountability as a small business owner, developing a broad skill set.
• Running a small business was likened to a "mini MBA" due to the diverse roles one must play.
• He learned to understand his core competencies and the importance of delegating tasks he was not passionate about.
• These lessons helped him manage a large company like Hootsuite, where he focuses on his strengths and hires specialists for other areas.
• Holmes has a working knowledge of finance but prefers to have a CFO and a finance team who are passionate about those aspects.

"Small businesses are fantastic because ultimately full accountability rolls up to you... I think what you do also learn out of it is what are your core competencies? What do you like doing the most?... I figured out the areas that I am passionate about and areas that I need to backfill and to get other specialists in."

This quote reflects on the comprehensive learning experience gained from running a small business, emphasizing the development of a holistic skill set and the importance of recognizing one's strengths and areas where delegation is beneficial.

• Humans have a wide array of passions and interests, which can be leveraged by finding the right people to fill gaps in expertise or enthusiasm.
• It's important to build a team where members can contribute their unique passions, especially in areas where you may not be as passionate.

"And so the great thing about humans is that there is somebody that's passionate about all sorts of different interests, everything on the planet, and you just need to find those people that get passionate about things that maybe you're not. And backfill those."

This quote emphasizes the diversity of human interests and the strategy of assembling a team where each member brings passion for different areas, enhancing the overall capabilities and covering any gaps in the team's collective expertise.

• Maintaining entrepreneurial spirit is crucial for business survival.
• Large organizations often implement systems and processes to protect their economic engines, which can stifle entrepreneurial thinking.
• Creating a separate division or space for innovation can help retain entrepreneurial culture.
• Allowing for less stringent compliance in innovative divisions encourages outside-the-box thinking.
• Launching internal startups can reignite the entrepreneurial process and foster empathy for customers.

"Yeah, well, I think when companies lose that entrepreneurial spark, that's the day that they start to die."

This quote highlights the importance of retaining a company's entrepreneurial spirit and suggests that losing it is the beginning of a company's decline.

"We started a labs division of our company. Everybody is responsible and accountable for some innovation."

By establishing a labs division, the company encourages innovation throughout its workforce, while also creating a specific team with more freedom to explore new ideas.

"I recently launched a little startup within Hootsuite that was to scratch my own back problem..."

Creating a startup within the company serves as a hands-on reminder of the entrepreneurial challenges and customer empathy, reinforcing the importance of understanding customer pain points.

• Fragmenting a large workforce into smaller units can help maintain entrepreneurial culture and improve communication and alignment.
• The Alphabet model is an example of creating smaller, more focused entities within a larger corporation.
• Sociological theories suggest that there are optimal group sizes for maintaining cohesion and effectiveness.

"Like the Alphabet concept. I think it's smart."

This quote supports the idea of breaking down a large organization into smaller, more manageable units to foster innovation and leadership.

"There's sociological theory, I can't remember who. It's an easy wiki around tribe sizes of kind of like 130..."

Referencing sociological theories about optimal group sizes, this quote suggests that there are natural limits to effective group sizes, which can inform how companies structure their workforce.

• Meetings are often criticized for being unproductive, yet they persist as a staple in business.
• To optimize meetings, it is important to evaluate the purpose, participants, and expected outcomes.
• Implementing a policy where employees can excuse themselves from meetings if they don't add or receive value can improve efficiency.
• Designating a secretary to take notes and ensure accountability for action items can enhance the productivity of meetings.

"It's so funny how many books, how many blog posts, how many podcasts talk about how much meetings suck and we're still there."

Acknowledging the universal frustration with unproductive meetings, this quote sets the stage for discussing ways to improve them.

"One of the things we have is a policy of if you don't feel like you're going to be adding value or the meeting isn't useful for you, you just excuse yourself."

This quote outlines a practical policy to prevent unnecessary attendance at meetings, thereby streamlining them and respecting employees' time.

"But who is the secretary who's keeping the key takeaways and creating accountability and notes out of the meeting?"

Emphasizing the importance of documentation and follow-through, this quote suggests that clear roles and responsibilities are essential for effective meetings.

• Discusses the importance of time constraints in meetings.
• References Katerina Fake's "four liter water meeting" hack as a humorous example to enforce time constraints.
• Emphasizes that not all meetings are worth the time without these constraints.

Capping time, putting time constraints on Katerina fake. I think she came up with this idea on the four liter water meeting. Everybody sits around and chugs water until somebody has to do a bio break.

This quote highlights a specific strategy to keep meetings short and focused by using a humorous technique to encourage participants to be concise.

• Discusses the challenge of deciding which features to develop and release.
• Highlights the use of customer feedback in product development, especially in a social media context where responses are immediate.
• Mentions the balance between rapid releases and substantial updates that cannot be released incrementally.
• Talks about the importance of distinguishing between adding new features and improving usability.

We do always try to get informed customer decision and feedback at the forefront of releasing new product. But sometimes when you're working with an agile and rapid release environment, you just want to get it out and let people play with it.

This quote underscores the company's approach to incorporating customer feedback while balancing the need for quick releases in an agile environment.

• Discusses the philosophy of releasing a product early versus waiting for perfection.
• Mentions Reed Hoffman's statement on shipping products early, even if they're not perfect.
• Talks about the responsibility to users as the user base grows, necessitating more stable and reliable updates.
• Describes strategies like dark launches, A/B testing, and beta releases to gather user feedback without impacting all customers.

Early days, you have nothing to risk. You are scrappy, you're iterating quick. You should be getting something out the door and testing that people are using it and loving it.

This quote reflects the belief in the importance of early product releases to test market fit and user engagement, despite the product not being perfect.

• Reflects on the fundraising experience during 2008-2009, considering it an alright time compared to other periods.
• Discusses the current trend towards profitability in the venture capital market.
• Shares personal fundraising experience, including the challenges faced due to the lack of local expertise in Vancouver and the competition with other startups in the same space.

So the time that we were fundraising, it was 2008 nine. In terms of the capital markets, I think that it was an all right time.

This quote provides context for the fundraising climate during the late 2000s and contrasts it with the speaker's perspective on current market conditions.

• Hootsuite differentiated itself from early competitors by focusing on building tools for businesses rather than a consumer-based social browser.
• The goal was to create a "Basecamp for social media," taking inspiration from 37signals' Basecamp products.
• Hootsuite's initial funding of $1.9 million helped the company become cash flow neutral within a year, indicating strong product-market fit.
• The company aimed to add more capital to increase growth velocity after establishing a sustainable economic model.

"They were more focused on building a social browser, a consumer based social browser. That wasn't our vision. We wanted to build tools for business." "We used our initial 1.9 million to get to cash flow neutral in about a year."

The quotes highlight Hootsuite's strategic focus on business tools rather than consumer applications and their efficient use of initial funding to achieve financial stability quickly.

• Ryan Holmes appreciates Mark Schuster for his effective use of social media platforms, starting with Twitter and moving on to Snapchat.
• Richard Branson is also recognized for his exceptional brand-building abilities on social media.

"You know who I always love is Mark Schuster. So when we first started getting going in Twitter 2008, nine, he was crushing it then. He's now crushing it on Snapchat and doing really interesting stuff." "Branson also is doing a great job building his brand and social."

These quotes exemplify the admiration for individuals who have successfully leveraged social media to enhance their presence and influence, serving as benchmarks for others in the industry.

• Ryan Holmes enjoys a variety of social platforms, appreciating the diversity of the ecosystem.
• "Media Redefined" is mentioned as a favorite newsletter, with a nod to Holmes' own newsletter.
• Holmes is bullish on Snapchat due to its large and engaged user base and its innovative features like Memories.
• He believes that Snapchat has significant growth potential.

"I love all of the social networks we work with. Twitter, Facebook, LinkedIn." "No. I'm hugely bullish on Snapchat. 10 billion views daily."

The quotes reflect Holmes' enthusiasm for multiple social networks and his particular optimism about Snapchat's future in the social media landscape.

• Hootsuite plans to continue supporting customers through the evolving landscape of social media interactions.
• Ryan Holmes envisions brands increasingly engaging with customers on social platforms throughout the entire customer journey.
• Hootsuite aims to facilitate the full customer experience, from discovery and marketing to sales and customer support.

"So whether it's from discovery, through marketing, through sales and social selling, or on the other end, customer support and creating customer advocates, that is where people are gravitating towards is social."

This quote summarizes the comprehensive approach Hootsuite intends to take in supporting brands' social media strategies, emphasizing the importance of customer engagement across all stages of interaction.

• Ryan Holmes sees the value in MBAs for certain individuals, though it was not the right path for him.
• He recommends the book "The Long Walk" for its portrayal of the human spirit's resilience.

"There's no right answer there. It's chocolate or vanilla." "It's called the Long Walk and it is a really great book about the human spirit ability to overcome adversity."

The quotes convey Holmes' perspective that educational paths are subjective and highlight his recommendation of a book that inspires perseverance and perspective on challenges.