20VC Why You Should Build Your Investor Team Like A Sports Team & How To Leverage The Abilities Of Your Investors Effectively with Ted Blosser, Founder & CEO @ WorkRamp

In this insightful episode of "20 Minutes VC," host Harry Stebbings interviews Ted Blosser, CEO and founder of Workramp, a startup revolutionizing employee training for companies like PayPal and Twilio. Blosser shares his journey from a failed first startup to learning from tech leaders at Box and ultimately addressing a significant pain point in employee development with Workramp. Key insights include the importance of brand building in enterprise, selecting investors like building a sports team, and the continuous pursuit of product-market fit. The conversation also touches on leveraging both short-term and long-term investor relationships, with Blosser emphasizing the role of diversity from a company's inception and the aspiration to organize enterprise knowledge over the next five years.

• Harry Stebbings introduces the podcast and the guest, Ted Blosser, founder and CEO of Workramp.
• Workramp is a startup that specializes in training and development for employees at companies like PayPal, Twilio, and Optimizely.
• Ted Blosser is a Y Combinator alumnus and a former early employee at Box, an enterprise powerhouse.
• The episode was made possible thanks to an introduction from Alexis Ohanian and Gary Tan at Initialized Capital.

"Well, today I'm delighted to be joined by Charlie Blossom, the founder and CEO of Workramp, the startup that's transforming how the best companies like PayPal, Twilio and optimizely train and develop their employees."

The quote introduces Ted Blosser and his company, Workramp, highlighting its role in employee training and development for notable tech companies.

• Ted Blosser discusses his first startup in his mid-twenties, which was a failure.
• He learned two key lessons: to learn from the best before starting another company and to work on something with true meaning and impact.
• After his initial failure, Ted moved to Silicon Valley and joined Box, where he learned how to build a hyper-growth business and identified a significant problem in employee development and training.
• The experience at Box led to the founding of Workramp, with a focus on helping enterprises develop their talent.

"Thing I learned from that was really twofold. One was that if I went to go start a company again, I would definitely go learn from the best before I went and started that company, really understood understand how to actually build a company from scratch. And then two is actually go work on something that had true meaning and impact."

Ted Blosser reflects on the lessons learned from his first startup's failure, emphasizing the importance of learning from successful leaders and focusing on meaningful problems.

• Ted Blosser shares insights from his time at Box, including the importance of leadership and execution.
• He observed Aaron Levy's ability to transform the enterprise content management market and make CIOs a target buyer demographic.
• Box's strategy involved heavy spending for customer acquisition to become the leading brand in the enterprise market.
• A strong sales team was critical to Box's success, demonstrating the need for both a great brand and excellent execution.

"One of the biggest strengths of box that not a lot of people know about is how good their sales team was. They had had sales leaders there for four to five years because that's the engine that really keeps that business going."

The quote highlights the significance of a robust sales team in driving Box's growth, pointing out the often-overlooked aspect of their success.

• Ted Blosser discusses the nuances of brand building in the enterprise sector.
• He points out that startups often misunderstand the process, and emphasizes the importance of market positioning and execution.
• Building an enterprise brand involves creating a market, educating buyers, and being the top choice for customers.
• The brand's value proposition must be clear, and the company needs to deliver on its promises to build a strong enterprise brand.

"I think that has also shown us how important it is to not just build a great brand, but also to execute extremely well on that brand."

Ted Blosser explains that a successful enterprise brand requires not only a compelling brand image but also the ability to execute and deliver on the brand's promise.## Importance of Brand in Enterprise Realm

• The best product does not guarantee company success in the enterprise sector.
• A well-trusted brand is considered more crucial than having the best product.
• Companies like Salesforce, Netsuite, SuccessFactors, and Concur have strong brands rather than the best products.
• Branding is a key component of a company's moat against competitors and in gaining customer trust.
• Investors like Gary Tan and Alexis Ohanian from Initialize have been instrumental in brand building.

"I think the companies that actually have both a good product. But even more important, the best brand will win if you look@salesforce.com they don't have the best product in the world, but they have the best brand."

This quote emphasizes that a strong brand can be more significant than the product quality in the enterprise market, using Salesforce as an example.

• Choosing investors should be akin to building a sports team with diverse skill sets.
• Each investor should bring a unique value or expertise to the company.
• Initialize was chosen for their understanding of consumer markets to apply those strategies to enterprise.
• The sports team analogy illustrates the need for different roles such as forwards, defenders, and midfielders, which in a company's context translates to different investor expertise.

"But I had a different mentor who actually said, look, Ted, you should actually approach this differently. Don't just look at it as a spouse you would look for, but really look at as a team you're building and think about the skill set that each VC brings to the table."

This quote suggests a strategic approach to selecting investors by considering the unique skills and value they bring, rather than just a long-term partnership.

• Every investor chosen has a specific purpose and contribution to the company's growth.
• Slack was brought on as an investor for their next-generation enterprise software expertise.
• Suse has been helpful in long-term strategy and institutional VC perspective.
• CEO coaches like Eli Gill and Adrian Un provide coaching from their experience.
• Charlie Songhurst brings enterprise knowledge from his time at Microsoft.
• The selection of investors is strategic and based on the specific benefits they offer.

"But every person we brought on, we said, look, where does this investor fit in and how can we leverage them to help us be successful in the future?"

This quote highlights the deliberate process of selecting investors based on where they fit into the company's future success strategy.

• Founders should be selective if there is demand but prioritize executing and getting funding if demand is low.
• Establish clear objectives for what you want from investors and the funding round.
• The approach to selecting investors may vary based on the company's position and goals.

"So our ultimate objective was to get the right investors and then two, get enough money to get us into the next round. And so I think you really lay out your objectives and then go tackle them from there."

The quote advises founders to set clear objectives for investor selection and fundraising to guide their approach.

• The team debated between an 18-month and a 24-month funding runway.
• Growth in revenues was a factor in determining the acceptable runway length.
• The decision was made to cap the raise at $1.8 million to impose constraints and ensure product-market fit before scaling.

"I would say we were aiming more for the 24 months on a conservative headcount level, and we actually did cap it."

This quote reveals the team's conservative approach to funding, aiming for a longer runway and capping the raise to encourage disciplined growth.

• Product market fit is considered a vague term with varying definitions.
• Different contexts and stories illustrate the concept of product market fit.

"I think product market fit is this vague term that almost everybody uses in a different context."

The quote reflects the ambiguity surrounding the concept of product market fit and its varied usage in the startup and VC community.## Continuous Pursuit of Growth

• Paul Graham's advice to YC companies emphasized the importance of never being satisfied and always seeking growth.
• Successful companies like Amazon, Airbnb, and Uber continue to invest in new areas despite having strong product-market fit.
• Growth is measured not just by revenue and customer acquisition but by the potential to increase the growth slope.

"None of you guys are at product market fit... don't be satisfied with wherever you're at. Always look for that next area of growth."

This quote by Paul Graham highlights the concept that achieving product-market fit is not an endpoint but a continuous process. Companies should constantly seek new growth opportunities.

• Ted Blosser shares a story about Aaron Levy of Box, emphasizing the importance of recognizing achievements but quickly shifting focus to future goals.
• Celebrating milestones is important, but it is equally crucial to set new objectives and work towards them.
• Reflection on past successes should be brief, with a focus on planning for the next steps to maintain momentum.

"Great quarter. But here's all the things we need to do over the next three to six months."

Aaron Levy's approach to balancing celebration with forward planning is encapsulated in this quote, illustrating the practice of acknowledging success while immediately setting the stage for future efforts.

• YC taught the importance of leveraging office hours with mentors to gain insights on various aspects of running a business.
• The peer network in YC fosters a competitive environment that drives companies to excel.
• Learning from successful partners and peers is crucial for understanding how to hire, build products, and acquire customers.

"You basically get to set up office hours with any of the successful partners or part-time partners, and you really get picked their brains on all aspects of the business."

Ted Blosser describes the value of mentorship and knowledge-sharing within YC, highlighting how access to experienced partners can significantly impact a startup's trajectory.

• A healthy balance between focusing on one's own goals and monitoring competitors is essential.
• Innovation should be prioritized over preoccupation with competitors, making bets that they are not considering.
• While keeping an eye on growth markets, it's important to also execute strategies that outperform competitors in daily operations.

"You really want to make bets that none of your competitors are even thinking about."

Ted Blosser emphasizes the need for innovation and the pursuit of unique growth opportunities without being overly focused on competitors.

• Seed investors should inherently be long-term focused, but some may not be, as evidenced by their due diligence processes.
• It's important to discern and avoid short-term focused investors and align with those who have a long-term perspective.
• Asusa Ventures is cited as an example of an investor that provides value in both the short and long term.

"Some definitely were not long term focused... You really want to just make sure you avoid the investors that aren't actually long term focused."

Ted Blosser discusses the importance of selecting investors who are committed to the long-term success of a company, as opposed to those fixated on immediate metrics.## Investor Approach

• Leo, a partner, focuses on long-term positioning over short-term revenue goals.
• Emphasizes the importance of product and team perspective for sustained growth.
• Encourages taking steps back if it leads to greater progress forward.

"He's always talked about making sure we're well positioned for the long term, both from a product's perspective, from a team perspective."

This quote highlights the investor's philosophy of prioritizing long-term strategic positioning over immediate financial gains, emphasizing product development and team building.

• Chad Byers focuses on "investor hygiene" during the seed phase for a solid Series A.
• Balances short-term preparation with long-term company goals.

"Chad Byers on the team, he'll do a really good job in terms of your investor hygiene, making sure that you're doing all the right steps during your seed phase to make sure you have a really solid series A."

The quote explains the role of Chad Byers in guiding the company through the necessary steps during early funding stages to ensure a successful transition to more significant investment rounds.

• Ted Blosser's favorite book is "The Last Lecture" by Randy Posh for its life-affirming message.
• Appreciates the grounding reminder of life's fragility and the importance of prioritizing what matters.

"Love that book because it keeps you well grounded in terms of, really, how fragile life is."

This quote reveals Ted's admiration for the book's message on the importance of recognizing life's fragility and focusing on what is truly important.

• Diversity should be considered from the start of a company.
• Actively sought a female founder for diverse opinions, resulting in immense success.

"We actively look to bring on female founder to our team, really, because we wanted that diverse set of opinions."

The quote signifies the proactive approach to diversity in the company's early stages, highlighting the value of varied perspectives for business success.

• Would choose to be CEO of Amazon, inspired by Jeff Bezos's passion for his work.
• Intrigued by the balance of stress and happiness in leading a major corporation.

"I would love to be Jeff Bezos and run Amazon."

This quote indicates Ted's curiosity about the experience of leading a large company like Amazon and understanding the factors contributing to Jeff Bezos's enthusiasm for his role.

• Recommends Paul Graham's essays for insightful content, despite less frequent updates.

"Those were definitely my favorite to read. Almost read every single word of them."

The quote conveys Ted's high regard for Paul Graham's essays, suggesting them as a valuable resource for readers.

• Prioritizes health-related resolutions after a near-death experience.
• Aims to maintain fitness and well-being amidst daily responsibilities.

"Actually had a totally random near death experience in 2016 over a weekend."

This quote underscores a personal incident that has influenced Ted's focus on health and well-being in his resolutions.

• Aspires to organize enterprise knowledge, similar to how Google organizes consumer information.
• The initial focus is on training and development within organizations.
• Aims to execute on this mission in the next five years.

"I think our goal is to organize all the knowledge within enterprises."

The quote outlines the ambitious goal of Workramp to become a central repository for enterprise knowledge, indicating a clear strategic direction for the company's future.

• Harry Stebbings thanks Gary and Alexis at Initialized Capital for introducing Ted.
• Harry promotes his Snapchat and academic writings for further engagement.
• Endorses Simba Hybrid for improved sleep and Cirrus Insight for enhanced productivity.

"I do also want to say a huge thank you to Gary and Alexis at initialized capital for the intro to Ted today, without which the show would not have been possible."

This quote expresses gratitude towards individuals who facilitated the podcast interview, highlighting the importance of networking and connections in the venture capital industry.

"And as I said earlier, one of mine is sleeping more. And that's where Simba hybrid comes in."

Harry shares his personal new year's resolution and endorses a product that aligns with his goals, providing listeners with a recommendation based on his experience.

"And there's no better for that than cirrus insight, the plugin for sales pros who use Gmail and outlook."

Harry recommends a tool aimed at improving productivity for sales professionals, suggesting its benefits based on its growth and customer feedback.