Fundraising Deep Dive with

Session Overview

Objective: Equip founders with a comprehensive understanding of their investment opportunity, assess risks systematically, evaluate investibility, reflect on strategic goals, receive actionable fundraising advice, and connect with mentors or investors for guidance.

Duration: 180 minutes (3 hours)

Target Audience: Early-stage startup founders (pre-seed or seed stage) seeking to raise capital.

Structure: The session is divided into seven segments, including breaks, to maintain focus and engagement.

Session Outline

1. Introduction and Context Setting (15 minutes)

Objective: Set the stage, align participants, and gather context about the startup.

Activities:

Founders deliver a 7-minute elevator pitch (problem, solution, market size, traction, funding ask).

Facilitator introduces the session’s goals, structure, and emphasis on risk assessment and mentorship.

Brief Q&A to clarify the startup’s objectives.

Deliverables:

Shared understanding of the startup’s goals and session expectations.

Timing: 0:00–0:15

2. Systematic Risk Evaluation Framework (45 minutes)

Objective: Assess risks across key dimensions (market, team, product, financial, execution) to identify potential pitfalls.

Activities:

Founders present data for each risk category (10 minutes).

Facilitator guides discussion to score each category (1–5 scale: 1 = High Risk, 5 = Low Risk) based on provided data (25 minutes).

Summarize risk profile and recommend mitigation strategies (10 minutes).

Deliverables:

Risk profile summary (e.g., “Market Risk: 4/5, Team Risk: 3/5”).

Specific recommendations (e.g., “Hire a CTO to address team risk”).

Timing: 0:15–1:00

3. Break (10 minutes)

Objective: Allow participants to refresh and process insights.

Activities: Informal networking or rest.

Timing: 1:00–1:10

4. Investibility Grading System (35 minutes)

Objective: Grade the deal’s attractiveness to investors based on risk, traction, narrative, and team appeal.

Activities:

Facilitator explains grading criteria (risk profile, traction, narrative strength, team appeal) (5 minutes).

Assign scores (1–5) for each criterion through discussion (20 minutes).

Calculate weighted average to determine final grade (A, B, C, D) and provide feedback (10 minutes).

Deliverables:

Investibility grade (e.g., “B, 72/100”) with breakdown (e.g., “Traction: 70, Narrative: 80”).

Feedback on strengths and areas for improvement.

Timing: 1:10–1:45

5. Personal Consideration of the Investment Opportunity (30 minutes)

Objective: Guide founders to reflect on the investment opportunity from investor and strategic perspectives.

Activities:

Facilitator leads a SWOT analysis (Strengths, Weaknesses, Opportunities, Threats) of the deal (15 minutes).

Discuss key questions: alignment with vision, investor fit, equity/control, risk tolerance (10 minutes).

Summarize a personalized decision framework (5 minutes).

Deliverables:

Decision framework (e.g., “Prioritize mission-aligned investors with industry expertise”).

Timing: 1:45–2:15

6. Break (10 minutes)

Objective: Provide a brief pause before the final segments.

Activities: Informal discussion or rest.

Timing: 2:15–2:25

7. Fundraising Advice and Best Practices (25 minutes)

Objective: Provide actionable strategies to maximize fundraising success.

Activities:

Facilitator shares tailored advice (e.g., build relationships early, craft a compelling pitch deck, leverage warm introductions) (15 minutes).

Discuss accelerators, investor due diligence, and risk mitigation plans (10 minutes).

Deliverables:

List of best practices (e.g., “Connect with investors 6–12 months before the raise”).

Recommendations for accelerators or tools (e.g., Y Combinator, LinkedIn).

Timing: 2:25–2:50

8. Introductions to Suitable Mentors/Investors (15 minutes)

Objective: Connect founders with two individuals for mentorship and potential investment.

Activities:

Facilitator presents profiles of two mentors/investors (e.g., Dr. Sarah Chen, healthtech angel; James Lee, gaming VC) (5 minutes).

Outline introduction plans (e.g., email drafts, suggested meeting formats) (5 minutes).

Discuss how to approach these relationships (5 minutes).

Deliverables:

Profiles of two mentors/investors with rationale for fit.

Draft introduction plan (e.g., “Email Dr. Chen with pitch deck and request a 30-minute call”).

Timing: 2:50–3:05

9. Q&A and Wrap-Up (15 minutes)

Objective: Address questions, summarize insights, and define next steps.

Activities:

Open Q&A on risk mitigation, investor outreach, or mentorship (10 minutes).

Recap key takeaways: risk profile, investibility grade, action items (3 minutes).

Outline follow-up: email with risk summary, pitch deck feedback, and introduction drafts within 48 hours (2 minutes).

Deliverables:

Clear action plan for founders.

I spend a lot of time thinking about what the world will look like in 10 years and what role I can play in creating that future and how I can help others do the same. My background is deep-tech and quantitative finance, but I've built a career as a pragmatic entrepreneur and investor with a knack for exposing lies perpetuated in monopolistic industries and building companies to right the wrongs. I spend most of my vocational time founding, funding, and advising mission-driven companies that are tackling big existential problems.

My first successful entrepreneurial endeavor was exposing the harsh truth that power tools can cut through any lock in just seconds: a reality purposefully concealed. I co-invented the SKUNKLOCK, the only bike lock that fights back with noxious chemicals to tackle this 10B+ global theft epidemic and pull the lid off a corrupted industry. SKUNKLOCK has since saved countless bikes and sparked the birth of the 1B+ deterrent lock industry.

More recently, my concern is the rapidly increasing wealth disparity and impending retirement crisis in America. There’s an estimated 7.1 trillion dollar deficit in retirement funds, social security is estimated to run out as early as 2034, and 40% of Americans are forced back into work every year. In 2022, outdated investing strategies (60/40 and MPT-driven robo-portfolios) experienced their worst performance in 100 years. The problem? Thousands of financial planners and educators, trusted by millions of investors, are not equipped with the tools, strategies, and compliance support they need to help their clients weather volatile markets and achieve financial freedom. This problem inspired Sidepocket, the only deep-tech investing platform-as-a-service solution empowering thousands of financial educators and planners with tactical strategies designed to weather down markets and achieve financial freedom more simply, safer, and sooner.

My work ethic and ethos are heavily influenced by my immigrant parents, who escaped communist Poland to find a better life. Entrepreneurs, especially immigrant entrepreneurs, are instrumental in creating a positive impact. I also enjoy empowering aspiring entrepreneurs by lecturing/mentoring at the Founder Institute, 500 Global, and the Alchemist Accelerator and helping deserving founders raise capital through American Pillar Partners and LvlUp Ventures (my seed stage venture fund).

I live by a few simple mantras: only criticize what you're willing to fix yourself; don't follow your passion, bring it with you; do things just because they're hard, there's less competition; and if you encounter analysis paralysis, get more data.

Looking forward to meeting you.