Investment Principal

Contrarian Thinking LLC; Austin (TX); On-site; USD 120,000 - 210,000; Full time

Benefits offered by this job

Health, dental & vision coverage

Unlimited PTO

401(k) plan with match

Direct deposit pay

Co-invest opportunities

Job summary

Contrarian Thinking Capital in Austin, TX seeks an investor who can own deal sourcing, underwriting, and supporting portfolio companies from diligence through growth. The role centers on building deal flow, crafting decisive memos, and collaborating with General Partners and the broader ecosystem.

The candidate thrives on fieldwork, has strong judgment, and can communicate clearly in written form to influence investment decisions. This is a full-time, in-office role in a small, startup-like team.

Qualifications

• Entrepreneurial background or experience with running a business.
• Strong modeling and underwriting abilities.
• Proven ability to generate deal flow and build relationships.
• Curiosity about unglamorous industries (e.g., waste management, HVAC).
• Independent judgment and ability to defend a position.
• Willingness to conduct fieldwork and outreach to founders.
• Clear writing and memo drafting skills.

Responsibilities

• Source and manage dealflow; own the pipeline end-to-end.
• Run due diligence from initial diligence to final memos.
• Craft memos that drive investment decisions for the partners.
• Support portfolio companies after funding and through growth phases.
• Collaborate with General Partners and cross-functional teams (media, community, events).

Skills

Deal sourcing

Diligence

Financial modeling

Memo writing

Field research

Networking

Judgment and conviction

Job description

Austin, TX | Full-Time, In Office

Position Overview

Contrarian Thinking Capital is an early-stage venture fund co-led by Christopher Petkas and Codie Sanchez. We invest in the real economy: the businesses that keep the lights on, move the freight, defend our shores, and maintain the infrastructure.

We're looking for an investor who can own the deal: sourcing, underwriting, and supporting the companies rebuilding the real economy.

This role is responsible for managing dealflow, running diligence end to end, crafting the memos that drive our investment decisions, and being a resource to our companies long after the wire clears.

This role is a partner track and sits at the center of the investment side of Contrarian Thinking Capital, working directly with both General Partners and alongside our media, community, and events teams- the parts of the ecosystem that make our sourcing advantage real.

What we're looking for

There is no single background that guarantees success in this role, and we are intentionally leaving fixed experience and pedigree requirements aside. That said, the people who tend to thrive in this seat share several traits:

• You have built or operated something. An entrepreneurial background is the strongest signal. If you have started a company, run a P&L, or carried real operational responsibility, you understand the businesses we back from the inside. Consulting or banking experience on top of that is a meaningful plus; it means you can also model, structure, and diligence with rigor.
• You can underwrite. You are comfortable in a model, fluent in unit economics and discerning the metrics that drive a business. You know the most important part of diligence is often the assumption everyone else took for granted.
• You generate dealflow. You build relationships that turn into pipeline, and founders want you on their cap table. You're the person founders call before they raise, not after.
• You are genuinely curious about unglamorous industries. Sectors like waste management, HVAC, metal fabrication, and facilities services interest you rather than bore you.
• You have judgment and conviction. You form independent views, you are willing to be the dissenting voice in the room, and you can defend a position without becoming attached to it.
• You do the fieldwork. You tour the facility, work through a founder's imperfect data room, or make twenty customer calls to get to the truth.
• You write and think clearly. A strong memo is an argument, not a data dump, and you can construct one with a clear and concise point of view.

Who You Are

• You’d rather be right than consensus, and you can sit with being early
• You do the fieldwork - the facility tour, the messy data room, the twenty customer calls
• You take ownership without waiting for permission or a process to follow
• You give and take direct feedback without it becoming personal
• You’re curious about how things work at the atomic level, especially the boring parts
• You want to build something in a small team where your judgment visibly moves the outcome

Why This Role Matters

We're seeing more opportunities than we can chase, diligence, and support. This role fixes that. You'll be the third voice in our investment decisions and the first point of contact for a meaningful share of what we see. The companies rebuilding the physical economy are getting funded right now, by someone. We'd like it to be us, and you to help make that true.

What is Contrarian Thinking?

Who we are: We are an investment and advisory firm powered by media and led by veterans of Wall Street, Private Equity, and the operators of Main Street businesses.

Our Ecosystem

1. Capital & Investment - We invest in businesses through diversified strategies, and support our portfolio in scaling to create enduring, profitable businesses.

2. Education & Advisory - We assist in the full cycle of acquiring and scaling businesses through our two cohorts: the Academy and the Boardroom. Our vetted platform of buyers and builders utilize our campus, curriculum, systems and advisors to buy, invest in, and scale businesses.

3. Events & Community - We produce nationwide events for buyers and builders with live workshops, chapter meetups, weekly calls, and annual conferences.

4. Media & Content - We aim to be the largest and most trusted business media company in the world through podcasts, YouTube, books, and online education.

Come build with us.

Location: Austin, TX - Full time in office.

Type of Employment: Full-Time

Crew Benefits

• 100% Company-paid health, dental, and vision for all full-time Crew Members with an option to add any dependents.
• Unlimited PTO Policy (with approval from your Direct Support) + 8 paid US holidays
• On-time direct deposit pay 2x-month
• Option to enroll in a 401(k) plan with competitive match options
• Employee-only co-invest opportunities