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.
"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.
"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.
"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.
"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
"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.
"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.
"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.
"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.
"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.
"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
"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.
"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.
"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.
"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.
"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
"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 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.
"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.
"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.
"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.
"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.
"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.
"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.
"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.