20VC How To Drop The BS and Relationship Build With Investors, What Investors Can vs Cannot Help Your Company With & Why When There Is Doubt There Is No Doubt In Hiring

In this episode of "20 minutes VC and Founders Friday," host Harry Stebbings interviews Jason Boehmig, the founder and CEO of Ironclad, a company revolutionizing legal contracting for modern legal teams. Jason, a former corporate attorney and adjunct professor of law, has impressively raised over $84 million for Ironclad, with a recent $50 million Series C round led by Ali Rowghani at YC Continuity. The conversation delves into Jason's passion for transforming the archaic contract process into the digital age, his vision for Ironclad, and how the legal profession can benefit from this innovation. They also discuss the importance of customer obsession in product development, the value of building a strong team early on, and the critical role of venture capitalists in a startup's journey. Jason's unique approach to leadership, his emphasis on aligning the company towards common goals, and his personal growth as a CEO are highlighted, showcasing his dedication to Ironclad's mission and the legal industry's future.

• Harry Stebbings hosts the 20 minutes VC and Founders Friday podcast.
• Harry has an Instagram presence at @hdebbings1996.
• The episode features Jason Boehmig, founder and CEO of Ironclad.
• Ironclad is a startup focused on legal contracting for modern legal teams.
• Jason Boehmig has raised over $84 million for Ironclad from notable investors.
• Ali Rowghani at YC Continuity led their recent $50 million Series C.
• Jason's background includes working as a corporate attorney and as an adjunct professor of law.
• Acknowledgments to Jesse at IA Ventures and Semil at Haystack for their question suggestions.

"You are listening to the 20 minutes VC and Founders Friday with me, Harry Stebbings at H debbings 90 96 with two b's on Instagram and it'd be great to see you there." "To date, Jason has raised over $84 million with ironclad from some of the best in the business, including Sequoia Excel, Greylock Emergence, IA Ventures, Semilshar's Haystack, and then obviously Ali Ralgani, who led their."

Harry introduces the podcast and highlights Jason Boehmig's achievements with Ironclad, including the successful fundraising efforts.

• Brex is highlighted as a corporate card for startups, reaching unicorn status quickly.
• Brex founders built it after facing challenges obtaining a corporate card in the US.
• Brex offers high limits, no personal liability, and rewards on various services.
• Pilot is introduced as a bookkeeping service for businesses, offering detailed financial reports and accrual basis bookkeeping.
• Dialpad is presented as a communication platform for teams, offering voice, video, messages, and meetings, with voice intelligence for customer conversation insights.

"Brex founders Henriquen Pedro built a payments business in Brazil but kept getting rejected for a corporate card in the states." "Pilot for bookkeeping gives you back the freedom to focus on your business." "Dialpad allows you to connect your team with a communications platform that powers voice, video messages and meetings across your existing devices."

Harry discusses the services provided by Brex, Pilot, and Dialpad, emphasizing their benefits for startups and businesses.

• Jason Boehmig was a corporate attorney and law professor before founding Ironclad.
• He is fascinated by contracts as a transformative technology for business.
• Jason sees the digital age as an opportunity to revolutionize how contracts are managed.
• He aims to help the legal profession by reducing low-level work and restoring advisory roles.
• Jason believes in the importance of contracts in business history and their potential for digital transformation.

"So for me, I've always been fascinated by the contract." "It's so obvious to me that we're going to move that into the digital age." "The legal profession has been in this crisis for the past couple of decades, really, and it's just getting worse year and year."

Jason expresses his deep interest in contracts and their significance in business, as well as his desire to improve the legal profession through digital advancements.

• Jason Boehmig has a background in Wall Street, which he finds somewhat cliché in Silicon Valley.
• His experience at Lehman Brothers taught him the importance of independent thought and managing psychology.
• He learned to think for himself and not take others' words at face value.
• This mindset helped him in the early days of Ironclad, especially when facing skepticism.
• Jason emphasizes the value of grit and independent analysis in his journey from Wall Street to founding Ironclad.

"I'm always a little embarrassed to have a Wall street background." "I realized that I sort of took everyone's word for what was going to happen, and that was, hey, it's all going to be fine." "So I think that that kind of grit really was something that I got out of that Wall street experience."

Jason reflects on his time at Lehman Brothers and how it shaped his approach to founding and leading Ironclad, stressing the importance of self-reliance and critical thinking.

• Jason Boehmig believes in learning from others but also in finding one's own path.
• He acknowledges that while some people are experts in their domains, innovation requires individuality.
• Jason's personal growth as a CEO involved embracing his introverted nature and finding his unique leadership style.
• He advises respecting others' accomplishments but also carving out a unique approach to innovation.

"I agree with you in that there's definitely people that know what they're doing in their space." "But I also do firmly believe you have to find your own way." "It's only as I've committed to finding my own way and my own molding of these different traits together that I felt more confident in my own personal journey there."

Jason discusses the balance between learning from others and forging a personal path in the startup world, emphasizing the importance of self-discovery in leadership and innovation.

• Emphasis on being obsessed with the customer to guide product development.
• Early strategy focused on serving local companies in Soma, San Francisco for direct feedback and rapid prototyping.
• Created a virtuous cycle of observing, prototyping, and immediate feedback.
• Geographic and target demographic constraints accelerated the product development process.

"And one of those timelessly good business principles is be as obsessed with your customer as you possibly can." "Let's be super intentional and let's deliberately try to work with companies that we can literally walk to their office." "So that rapid iteration and actually constraining ourselves to a really small geographic area, I think helped us move a lot faster than companies that are trying to go on a much larger scope right from the beginning."

The quotes emphasize the importance of customer obsession and the strategic decision to focus on a small, local market for immediate feedback and rapid iteration, which Jason believes is a timelessly good business principle.

• Curiosity and a deep understanding of customer problems are key.
• Ironclad focused on building a comprehensive system for all contracts within companies, specifically targeting legal teams.
• Leveraging constraints and curiosity to validate insights across multiple customers.
• The process helped to avoid potential mistakes and accelerated learning despite lack of experience in technology.

"Yeah, I think it really does come down to just pure raw curiosity and wanting to understand that problem better than anyone else." "So I think putting ourselves within those constraints and being genuinely curious, it just takes care of so many wrong turns."

Jason highlights the significance of curiosity in understanding customer needs and how setting constraints can streamline the process and reduce the likelihood of making mistakes.

• Early-stage companies should pay attention to frustrated users as they can be turned into champions.
• Frustration indicates strong user interest and provides valuable feedback for product improvement.
• The balance between data and intuition is critical in product development decisions.

"And we had that from pretty early on. So I don't know if I have good advice on how to get to the point of frustration with your user, but I know that you need to really lean into early frustrated users because that's where you can really turn them into champions and where you really get the best possible source of information."

Jason discusses how early frustration from users is a positive sign and can be leveraged to improve the product and build strong user relationships.

• Early customer base was tech-heavy, but Ironclad's focus on contracts made it easier to diversify.
• The legal teams across different industries face similar challenges, making the product relevant beyond the tech sector.
• Ironclad's focus on the legal vertical may provide resilience during economic downturns due to the countercyclical nature of the legal industry.

"And I actually think that's a unique thing about contracts, is if you look at the legal team at Dropbox and you look at the legal team at L'Oreal and you look at the legal team at some of these professional sports teams that we work with, they're all very similar." "So I'm excited to see how ironclad fares during the next cycle."

Jason explains how Ironclad's focus on contracts allows for easier customer diversification and potentially provides stability during economic downturns due to the commonalities in legal team challenges across industries.

• Early-stage startup recruiting is challenging and often relies on personal networks.
• Co-founder's reputation and connections can attract early employees.
• The early team can create a snowball effect, attracting more talent.
• Ironclad looks for a "laid back, intense" culture fit over pedigree.

"But when I look at our first employee, it was somebody that Kai worked with. And basically the calculus on her end was, I love working with Kai, and I don't even care what he's working on." "So we've kind of assembled this band of misfits in the early days that attracted some other like-minded misfit and went from there."

Jason discusses the importance of co-founder networks in early hiring and how Ironclad's unique culture has shaped its team-building approach, valuing cultural fit and intensity over traditional credentials.

• Toby, an employee without a college degree, started at an entry-level position and rose to lead the support function through demonstrated competence and motivation.
• The speaker emphasizes the value of allowing individuals to prove their work caliber, suggesting that early-stage consulting agreements or trial periods can be beneficial.
• A culture of thoughtfulness, humility, and motivation is highlighted as pivotal for employee development and cultural leadership within the company.

ght after Toby doesn't have a college degree, started doing data entry for us for, I think, $10 an hour and was so thoughtful and humble and motivated and competent at doing that that we just kept giving her more work. Now she is running our entire support function at the company and has just been this incredible cultural leader.

This quote illustrates the speaker's belief in meritocracy and the potential for individuals to advance within a company based on their performance and attitude, regardless of formal education.

• The advice "when there's doubt, there's no doubt" is applied to the hiring process, suggesting that any hesitation about a candidate may be a sign not to proceed.
• The speaker asserts that a hiring decision should only be made when there is complete certainty and a sense of potential loss if the candidate does not join.
• This approach to hiring is maintained even as the company grows, with the speaker's company now having 125 employees.

If you have an iota of doubt in the hiring process and you feel like you could not be that disappointed if this person didn't join anytime that we haven't gotten to complete certainty, I think is a mistake and you should almost be heartbroken if the person doesn't want to join your company.

The quote conveys the speaker's hiring philosophy that one should only extend an offer to a candidate if their absence would be keenly felt, indicating a high level of commitment and belief in the candidate's fit with the company.

• The speaker views curiosity as a key trait for understanding customer problems and for personal growth as a CEO.
• Learning about every function within the company is seen as an exciting aspect of the CEO role.
• A great CEO is characterized as someone who aligns disparate parts of the company and ensures effective communication and empowerment across teams.
• The speaker prefers a collaborative and educational leadership style over a domineering or visionary one.

I love just connecting these dots between other areas that don't normally talk to each other. And as I've learned more and more about the CEO role, I do think that one flavor of a great CEO is one that takes all of these disparate parts of the company and makes sure that they're interacting, the right information is flowing and that all of the arrows are pointing in the same direction at the company.

This quote reflects the speaker's enjoyment in fostering interdepartmental connections and alignment within the company, which they consider an essential aspect of effective leadership.

• The speaker believes that honesty and vulnerability are critical for a leader, especially for founders who are new to their roles.
• Admitting the need for and hiring people who are more skilled in particular functions is key to the company's success.
• Ironclad's reputation for having an exceptional leadership team is attributed to this approach of acknowledging one's limitations and focusing on team empowerment.

And part of the reason I think we've been able to attract incredible talent is just admitting that and letting go of the pretense that I'm a great sales leader, or I'm a great customer success leader, or I'm a great marketing leader.

This quote emphasizes the importance of self-awareness and the willingness to admit one's areas of weakness as a leader, which in turn helps to attract and empower talented individuals in those areas.

• The speaker values personal enjoyment and curiosity when building relationships with venture capitalists (VCs).
• He highlights the importance of connecting with like-minded individuals who share a passion for developing great companies.
• The speaker sees board members as integral parts of the team and puts significant effort into their selection.
• Personal anecdotes about engaging with VCs underscore the importance of culture and shared values in the investment process.

my whole philosophy on this has just been, life is too short to work with people that you just don't really enjoy being around.

This quote encapsulates the speaker's philosophy of working with people who are not only professionally competent but also personally enjoyable to be around, suggesting that this extends to relationships with VCs.

• The speaker advises founders not to overlook the importance of legal terms during investment negotiations.
• He recommends taking time to have a lawyer review term sheets and to choose a lawyer whose advice is valued.
• The speaker underscores the value of legal counsel in avoiding potential pitfalls in the investment process.

So if I'm talking to other founders, I would say don't discount the importance of the legal terms.

This quote advises founders to pay attention to the legal aspects of investment negotiations, emphasizing the need for careful review and professional legal advice to protect their interests.

• The speaker believes that VCs can provide valuable pre-investment support through customer introductions and insights into the market.
• Authentic relationships with VCs can lead to mutually beneficial outcomes, such as closing deals with dream accounts.
• The speaker suggests that founders should test the value-add of potential investors and spend time genuinely getting to know them.
• There are misconceptions about the kind of value VCs can bring, which the speaker hints will be discussed further.

We recently did our series C round with Y Combinator continuity fund, and we've obviously known Y combinator for years now at this point. But Ali was so incredibly helpful with thoughtfully picking out some right customer intros and helping guide us through that process.

This quote provides a specific example of how VCs can add value beyond capital by facilitating strategic customer introductions and offering guidance, demonstrating the practical benefits of a strong investor-founder relationship.

• Personal interactions are critical when working with venture capitalists (VCs) over long periods.
• Knowing people in advance of funding rounds can lead to more meaningful dialogues that can't be forced.
• The process of getting to know each other allows for a better understanding of the individuals involved, beyond just the business.

"more few sessions where it was just like, hey, we love the business, but we're not going to really talk about like, who are you and what's going on with you, and tell me more about you as a person, since we're going to work so deeply together over a very long time horizon."

This quote emphasizes the importance of personal relationships in business, particularly in the context of venture capital investment, where the partnership is likely to be long-term.

• Fundraising can serve a dual purpose of acquiring customers and being part of the due diligence process for VCs.
• It's important to recognize the multifaceted benefits of fundraising beyond just securing financial investment.

"I wish you could see my face. I'm totally smiling now at both the really personal element that you mentioned there, but also the using fundraising for customer acquisition."

The speaker is expressing agreement and pleasure at the notion that fundraising is not only about raising money but can also be an opportunity to win customers.

• VCs cannot and should not make critical business decisions for founders.
• Founders should rely on their own judgment and work, even if they respect the experience of a VC.
• Great VCs understand their role and avoid overstepping, supporting founders without driving decisions.

"Yeah, I think it goes back to that intellectual rigor before, is a VC can't make a critical business decision for you."

This quote underlines the belief that while VCs can provide guidance and support, the ultimate responsibility for critical business decisions lies with the founders themselves.

• Prestigious investors can be both intimidating and inspiring for founders.
• Smart investors can still be wrong, highlighting the importance of humility and collaborative problem-solving.
• Founders should maintain their own direction and decision-making without undue pressure from investors.

"I mean it is on one hand, yes, it's pretty amazing. And every time I kind of walk into the Excel sequoia office and even saw ironclad's logo kind of go up on the logo board at Excel the other week and it's just like, oh my goodness, I can't even believe that that's happening."

This quote reflects the awe and pride a founder may feel when seeing their company recognized by a prestigious investment firm.

• Early support from visionary investors can bolster a founder's conviction, especially when the business is not yet widely recognized.
• Developing conviction in the early stages can be crucial for long-term success.

"But we did spend a couple years in such a backwater with so few people caring about what we were doing that I also think it developed some conviction that once people actually come around."

The speaker is acknowledging the importance of having strong belief in one's business, especially during phases when it is not in the limelight.

• "Meditations" by Marcus Aurelius is appreciated for its raw, unfiltered insights into philosophy and leadership.
• Hiring is the most critical activity for a company, and it is beneficial to invest time in knowing potential hires well in advance.
• DJing is likened to software development, with modern tools enabling greater accessibility and efficiency.

"Such a hard question because I'm reading all the time. I'm going to go with a book on my desk right now. Meditations. Marcus Aurelius."

This quote reveals the speaker's current reading choice and implies the value of timeless wisdom in leadership and personal development.

• "The Checklist Manifesto" inspired the creation of Ironclad, emphasizing the power of checklists to ensure consistency and quality in routine work.
• Ironclad's user interface incorporates checklists as a core feature, reflecting the book's influence.

"Arguably the inspiration for ironclad. So, the checklist manifesto, incredible book, I believe Ted introduced it to me when I was working at Fenwick."

The speaker credits "The Checklist Manifesto" as a significant influence on the founding and design principles of their company, Ironclad.

• The goal for the next five years is to continue building and maintaining a customer-focused approach.
• Ironclad aims to become the central hub for business contracts for companies worldwide.

"So keep building, always keep our nose to the grindstone, keep being obsessed with the customer, keep the focus on hiring, and we want to become the most important vendor that our customers use."

The speaker outlines Ironclad's commitment to growth, customer service, and becoming a key player in the business contracts space.

• The speaker expresses gratitude for the opportunity to participate in the podcast and appreciates the host's authenticity.

"Thanks so much, Harry. It's been a real pleasure to be on this podcast. I really appreciate what you're doing and the authenticity and genuineness which you're bringing to it."

This quote shows the speaker's appreciation for the genuine nature of the podcast and the value of such discussions in the industry.