Get ready for a spicy conversation about disrupting outdated construction practices, navigating diversity compliance requirements in government contracts, and building an innovative B2B marketplace. In this candid interview, Sherveen speaks with Wissam Akra, founder & CEO of Tough Leaf, about how his platform is transforming the way general contractors find and hire small, diverse, and minority-owned businesses for major public and private infrastructure projects.

From tackling compliance headaches and navigating shifting political + DEI landscapes, to the nitty-gritty of building a SaaS marketplace that scrapes data from countless government databases, Wissam shares how Tough Leaf is removing barriers for subcontractors nationwide. The two also get into the thorny topic of union bosses resisting automation, the reality of tech adoption in construction, and why a capitalistic solution can still advance social good. If you’re curious about construction tech, compliance automation, or how startups can disrupt traditional industries, this discussion is for you.

This is Episode 014 of The Sherveen Show!

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In a job search in tech? You've seen Sherveen talking about the latest in business and society on The Sherveen Show, on stage giving startup founders feedback on The Feedback Loop, and having deep dive tech and foundership conversations on Three Course Founders...

But he's also the founder/CEO of Free Agency and, since 2019, has helped hundreds of candidates in tech win over $400M in offers – he knows job search, and now you can learn it from him, too. For those in an active search (or who will be in the next 6 months), Breakthrough Job Search is a cohort-based course for tech industry professionals looking for an edge in this historically challenging job market. Enroll: https://www.freeagency.com/breakthrough

Follow Sherveen on X: https://www.x.com/sherveen

Follow Sherveen on LinkedIn: https://www.linkedin.com/in/sherveenm

Follow Wissam: https://www.linkedin.com/in/mwakra

We cover:

Union Bosses & Automation Backlash: Why some labor groups resist new technology and how it affects the U.S. economy.

Construction Tech & SaaS Solutions: The 25-year-old methods that Tough Leaf is replacing with a data-driven, AI-matching approach.

Navigating DEI & Compliance: How government mandates for small, women-owned, and minority-owned businesses create both challenges and opportunities.

Public vs. Private Projects: The difference in compliance requirements and incentives for Amazon, Meta, and other large private players.

Marketplace Pivots: Why the original “pure marketplace” model didn’t work—and how Tough Leaf found product-market fit with a more managed approach.

Politics & Tech: How pendulum swings in public opinion, from Reagan to Trump, affect regulation, procurement, and DEI programs.

Founder Insights: Balancing risk, trust-building, and pricing models (SaaS vs. outcomes-based) while trying to scale nationwide.

It's about: construction tech, diversity in the tech and startup workforce, minority-owned businesses, tech adoption in a legacy industry, venture capital, artificial intelligence, and so much more.

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