Building with Efficiency in the Age of AI

Welcome to Angel Investing Demystified - a newsletter that peels the curtain back on Angel Investing, Venture Capital, and Startups.

Each edition, you’ll get a 5-minute recap of one of our weekly virtual events held at Angel Squad. These sessions include anything from fireside chats to interactive deal reviews and workshops from the top investors + operators in the game.?

Before we get into this week’s post, I’ve got a big announcement to share for those based in New York…

The NY tech scene is on fire, and if you’re not angel investing yet, it might be time to rethink that.

So, to build on this momentum, the team at Hustle Fund is hosting an Angel Investing 101 Bootcamp specifically for startup enthusiasts in New York that want to get up to speed - fast.

• What: 1-hour virtual event
• When: Tuesday, February 25th from 1:00 PM - 2:00 PM (ET)
• How: Live educational content, including a Shark Tank-style pitch event
• Cost: Free

Learn more and sign up here. Spots are limited!

With that, let’s jump into Edition #7: Building with Efficiency in the Age of AI

Event Overview

The professional landscape is undergoing a seismic shift, driven by the convergence of remote work, freelance opportunities, and AI-enhanced productivity. These trends are not just reshaping how we work but also the infrastructure supporting that work. At the forefront of this evolution is Contra , a platform designed for independent workers, which has emerged as a compelling case study in navigating and capitalizing on these trends.

Recently, we hosted a workshop for the Angel Squad community where Ben Huffman , Co-Founder and CEO at Contra, gave an eye-opening look into how AI is changing the landscape for knowledge workers.

Whether you’re an investor, operator, or anything in between, this session was packed with insights on how to prepare for the future of work.

Shifting Professional Dynamics: Beyond LinkedIn and Upwork

Traditional platforms like LinkedIn and Upwork, while instrumental in earlier phases of digital networking, are increasingly misaligned with the emerging needs of today’s workforce. As Ben observed, these platforms focus more on resumes and roles than skills and outcomes.?

“LinkedIn tells you what someone has done, not what they’re capable of doing,” he explained. This gap inspired Contra’s creation: a skills-first network enabling independent professionals to showcase their capabilities, without the friction of high commissions or poorly integrated commerce tools.

This vision was initially met with skepticism, with investors questioning the viability of a zero-commission freelancer marketplace. However, the pandemic catalyzed a paradigm shift. “COVID proved that remote and independent work isn’t just viable; it’s foundational to the future of work,” Ben said. This realization turned Contra from an unproven concept into a promising solution for a rapidly evolving workforce.

The 'Pain Cave': Growth Through Adversity

The journey to Contra’s current position was far from linear. Ben described the company’s early years, particularly 2022, as the "pain cave.” Metrics stagnated, morale fluctuated, and the company grappled with scaling challenges.?

At one point, Contra grew to 54 employees but struggled to maintain focus and efficiency. “You start drinking your own Kool-Aid,” Ben admitted, “and suddenly you have 10 projects that should be three.”

This period of adversity forced the team to reassess its approach. By 2023, Contra had streamlined to 27 full-time employees while leveraging over 100 independent contractors through its own platform. This hybrid model enabled the company to remain agile, focusing on core product development while outsourcing specialized tasks like design and content creation.

One striking example was the development of a company deck—crafted by a freelance designer on Contra and enhanced with AI-generated visuals. This "project-based structure" epitomizes Contra’s ethos of blending human creativity with AI efficiency.

AI’s Role in Scaling and Streamlining

Artificial intelligence has been a pivotal enabler in Contra’s journey. From content moderation to fraud detection, AI tools have automated labor-intensive tasks, allowing the team to focus on higher-value activities. For instance, Contra’s AI systems review and approve invoices, flagging anomalies for manual inspection only when necessary.

“AI gives everyone superpowers,” Ben remarked. By integrating AI into workflows, Contra has achieved what many startups aspire to: scalability without the bloat. This balance of technology and human judgment has become a cornerstone of its strategy.

Rethinking Work Models: Lessons for Analysts

Contra’s trajectory offers valuable insights into the future of work:

1. Hybrid Workforces as the Norm: Companies like Contra demonstrate the viability of combining a lean core team with a network of skilled independent contractors. This approach is not only cost-effective but also provides flexibility to scale resources as needed.
2. AI as a Strategic Amplifier: Effective use of AI can transform operations, automating routine tasks while enhancing decision-making processes. For organizations, this means prioritizing AI adoption where it adds clear value.
3. Skills Over Roles: The shift towards skills-based networks reflects a broader trend in professional development. Employers and platforms must adapt to emphasize demonstrable outcomes and competencies rather than static resumes.
4. Curated Experiences: By reducing spam and fostering meaningful interactions, Contra’s platform addresses a major pain point in professional networking. This underscores the importance of user-centric design in building sustainable networks.

Building Towards the Future

Looking ahead, Contra is doubling down on the future of knowledge work. Its evolving platform includes social layers to facilitate networking, tools for freelancers to promote their brands, and integrations with AI to further enhance productivity.

As Ben put it, “You’re only as good as your users say you are.” While things are rapidly changing, Contra’s story shows that adaptability, focus, and a relentless commitment to user needs remain as pillars when building in the age of AI.

And…that’s it for edition #7 of Angel Investing Demystified!?

If you’re a startup enthusiast in New York, don’t forget to check out our Angel Investing 101 Bootcamp that’s coming up. You’ll get an on-ramp to start your angel investing journey (and learn why right now is the time that VCs are doubling down on NY). Spots are filling up!

Disclaimer: All “Angel Investing Demystified” content is for informational purposes only, and should not be construed as legal, tax, investment, financial, or other advice.