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Taxes and Exits
Taxes and Exits episodes
- Perfecting the Elevator Pitch
In this episode, Andrew Ackerman shares expert insights on prospecting for investors, emphasizing active hunting strategies, effective outreach, and building meaningful relationships to secure funding. Perfect for startups and entrepreneurs looking to refine their fundraising approach.
Timestamps00:00 Introduction and episode overview
01:11 Andrew Ackerman's background and experience
04:56 Starting with 50-100 relevant investors
08:40 Researching investors and their portfolio companies
13:09 Using tools like Crunchbase and LinkedIn
18:22 Prioritizing investor lists: A, B, and C prospects
20:47 Handling portfolio conflicts and direct competitors
23:37 Approaching investors with warm introductions
33:44 Crafting effective outreach scripts and emails
42:28 Filling the investor funnel and managing follow-ups
44:28 Maintaining ongoing conversations and relationship management
48:16 Closing thoughts on fundraising and relationship building
56 min - Why Most Business Partnerships Fail and How to Avoid Being Next
In this episode, Ash Patel shares invaluable lessons from his extensive experience in business partnerships, real estate, and entrepreneurship. Discover how to find the right partners, draft effective agreements, and navigate the complexities of business breakups while maintaining friendships.
Timeline00:00 The Importance of Business Partnerships
05:59 Lessons from Early Partnerships
12:01 Navigating Partnership Dynamics
17:46 Creating Effective Operating Agreements
23:59 Evaluating Partnership Compatibility
29:40 The Role of Personal Relationships in Business
30 min - AI Risks Small Businesses Overlook: How to Avoid Costly Mistakes
In this insightful interview, Paul Graham and David Robinson explore the critical risks and strategic considerations for small and mid-sized businesses adopting AI technology. They discuss how to identify real problems versus symptoms, the importance of outcome-based delivery, and how to choose the right technology partners to ensure successful digital transformation.
Timeline00:00 Navigating Technology in Business
02:54 Understanding AI Risks and Opportunities
05:53 The Importance of Technical Talent
08:38 Identifying Hidden Risks in Technology
11:54 Outcome-Based Development Strategies
14:42 The Role of Managed Service Providers
17:47 Choosing the Right Technology Partner
20:58 The Mindset of Successful Entrepreneurs
23:34 Diagnosing Business Problems
26:47 Connecting with the Right Solutions
32 min - Unlocking $22.1m in Stalled Pipeline
In this episode, Jen Kelly shares how a company unlocked $22 million in pipeline by refining lead nurturing and sales strategies. Paul Graham discusses growth mindset, customer diversification, and effective marketing tactics for business success.
Timeline00:00 Introduction to Taxes and Exits
00:27 The mindset around growing and selling a company
01:24 Jen Kelly shares a $22 million pipeline success story
02:18 The importance of nurturing existing leads
03:24 Challenges in scaling from small to medium business
04:42 Creating a revenue engine and ideal customer focus
05:41 Risks of overexposure to key clients
07:00 Diversifying customer base and asking for feedback
08:31 Using third-party feedback to improve offerings
12:02 Effective lead nurturing strategies
13:32 Qualifying and re-engaging old leads
16:10 Offering short-term paid pilots to qualify clients
17:37 Vetting marketing agencies with small trials
19:24 Understanding marketing services and setting expectations
23:28 Tracking data and metrics for growth
24:49 Aligning marketing activities with business goals
28:56 Curiosity and resourcefulness in business growth
32:03 The importance of service over sales
33:01 Connecting with Jen Kelly and her company
34 min - Why Doing Everything Yourself Cost $100 Million
Larry G. Dix II shares his transformative journey of self-awareness, the importance of delegation, accountability, and living intentionally to maximize success and fulfillment in business and life.
Timeline
00:00 Introduction and the importance of self-awareness
02:08 Larry's journey of self-discovery and psychological profiling
04:05 The realization of being a visionary and the need for an integrator
07:12 The role of discipline, routines, and energy in success
12:06 Building a support system and accountability partners
17:17 The importance of living with purpose and legacy
28:53 Involving family and creating meaningful memories
37:06 Mastering morning routines and setting the tone for the day
45:44 Living authentically and the value of true friendships
52 min - The Power of Fractional CFOs in Scaling Your Business
In this episode, Paul Graham and Richard Boyd discuss the critical role of financial management and fractional CFOs in scaling businesses from five to thirty million dollars. They explore real-world stories, misconceptions about CFOs, and how AI is transforming finance functions, providing actionable insights for business owners aiming for growth and stability.
Chapters00:00 Navigating Financial Challenges for Business Owners
03:11 Real Stories of Business Financial Struggles
07:34 The Role of a Fractional CFO
13:12 Misconceptions About CFOs
19:42 The Impact of AI on Finance
25:27 Emotional Aspects of Financial Decisions
32:09 Scaling from Five to Thirty Million
39:39 Untitled design (1).mp4
40 min - The End of Manual Capital Raising
In this episode, Paul sits down with Elisabeth Bykoff ex-PwC, 10-year venture veteran, and founder of Boxsy, to break down why most founders start the fundraising process completely wrong, whether you actually need to raise at all, and how an AI COO platform is helping first-time founders get operationally ready before they ever talk to their first investor.
Timestamps
[00:00] Why fundraising becomes a full-time distraction for founders
[01:26] Elisabeth's origin story and how Boxsy was built
[04:01] Who the platform is for: first-time founders raising in 30 to 60 days
[07:00] Do you actually need to raise? Non-dilutive alternatives first
[09:27] How long fundraising really takes — and what shortens the timeline
[10:55] Why operational readiness is what investors expect now
[13:29] Inside Boxsy: 150K investor contacts, pipeline, and pre-built data room
[17:41] The control center: auto-pull metrics from HubSpot, QuickBooks, and your bank
[21:47] The real mission: changing the % of founders who make it to Series A
[25:40] Why the Zuckerberg path is 0.1% — and what success really looks like
[27:59] Creative runway strategies: consulting, equity crowdfunding, and staying scrappy
33 min - Before You Build a Family Office, Fix This First
JD Rockefeller invented the family office in 1882 because every advisor he had was working in a silo and nobody was talking to each other.
Most business owners today have the exact same problem.
Dale Montgomery oversees a virtual family office with 70+ specialists across tax, legal, wealth, risk, and business advisory. In this episode, he and Paul break down who actually needs one, what it costs, and what changes when you stop trying to hold it all together yourself.
📋 Timestamps
[00:00] Why most business owners think family offices aren't for them
[01:55] The origin story: Rockefeller, 1882, and why collaboration changes everything
[03:00] What Oprah, Gates, and the Waltons pay — and how the virtual model brings it down
[04:16] The five areas every virtual family office covers
[06:47] The one book every business owner should read before hiring anyone
[09:57] How long it takes entrepreneurs to trust having a team around them
[12:23] What the diagnostic process looks like on day one
[13:10] The general contractor analogy — and why it changes how you think about this
[20:18] Tax specialists inside the family office: oil & gas, solar, charitable deductions and more
[22:06] Pricing: $3,600, $5,800, or fully custom — what each level includes
[23:07] The $1M gross revenue benchmark and who should start exploring this now
26 min - The Hidden Cost of Not Tracking Your Digital Assets
An advisor came to Perry Woodin and said his client had 50 crypto wallets.
When they looked closer, they found 150. With dozens of digital assets across them that the client didn't even know existed.
Perry Woodin is the co-founder of Node40, a digital asset data company that has been reconciling crypto portfolios since 2015, before almost anyone cared about financial reporting in this space. In this episode, he and Paul break down why this is the first year crypto holders are actually required to report accurately, what the IRS letter looks like when something doesn't match, and how having detailed records opens up strategies most investors don't even know are available.
In this episode:
[00:00] What digital assets actually are from Bitcoin to tokenized real estate
[00:43] Who Node40 works with: high net worth individuals, crypto-native companies, and public companies
[01:56] Why 2025 is the first year everyone was required to accurately report crypto activity
[02:30] The 1099-DA explained and why 90% of them will have a mismatch
[03:36] What the IRS CP2000 letter means and what happens if you don't respond
[04:24] The individual investor pain point: wallets they forgot, assets they didn't know existed
[05:41] The 50-wallet client who actually had 150 and what was hiding in the other 100
[06:27] Why the burden shifts from individual to company to public company and what changes at each level
[07:29] Penalties explained: late filing, under-reporting, multi-state exposure, and public company risk
[07:55] When should you stop doing this yourself? The line between manageable and flirting with disaster
[08:24] If you've only used one exchange like Coinbase, you're probably fine here's when that changes
[09:17] What Node40 actually does: data collection, cost basis assignment, full asset lifecycle tracking
[10:20] How gifting crypto through a will or trust works — and why cost basis matters at time of passing
[11:17] Can you go back to 2010 or 2015 and reconstruct your entire crypto history? The answer might surprise you
[12:09] How CPAs and registered investment advisors use Node40 data for tax strategy not just compliance
[13:06] Tax lot strategy: how to choose which crypto assets to sell, gift, or borrow against to minimize tax
[14:05] Why borrowing against your lowest-basis asset beats selling and how to think about it like your portfolio
[15:22] Why Node40 never touches or holds your assets — they're purely a data company
[15:50] Advanced use case: covered calls, puts, and straddles on digital assets why accurate records make this possible
[16:39] The Node40 origin story: started as a staking company in 2015, pivoted to analytics in 2020
[17:37] Why most competitors just give you a number — and why Node40 shows you exactly how they got there
[20:04] What onboarding actually looks like: from two-hour self-serve to complex enterprise build-outs
[21:32] How automating business rules closes books faster and eliminates costly manual errors
[24:30] The right time to reach out and why waiting until tax season makes everything more expensive
27 min - How To Add AI To Your Business Without Breaking Everything That Already Works
It's not a magic robot. It's an LLM call on a while loop.
Mike Vanamburg has built AI agents for companies across industries — from cannabis dispensaries to bookkeeping firms to his own business — and the lesson he keeps learning is the same every time: start with the human, not the technology.
In this episode, Mike and Paul break down the real blueprint for integrating AI into a business, why fully autonomous agents always fail, what the difference between a workflow and an agent actually is, and what work might look like in ten years for the people who get this right.
In this episode:
[00:00] Why most people are approaching AI adoption completely backwards
[00:55] Start here before building anything: map the human workflow first, then add AI
[02:08] How customer journey mapping and process flow audits expose what you didn't know you were doing
[04:11] Should you use AI for the customer or for internal operations first? Mike's answer
[04:30] How one company replaced a multi-month competitor research process with a two-minute AI agent
[05:55] Why three clicks is now too much friction — and what chat-based UI is replacing it with
[07:01] Big companies vs. small companies: how AI implementation looks completely different at each size
[08:44] Are AI tools raising output standards or just giving people more time back? What Mike is actually seeing
[09:45] The three types of clients: step away more, do 10X more, or just meet the new standard of excellence
[10:27] The most unexpected challenge with AI implementation: it's always the people
[11:54] Why you have to ask clarifying questions before you build a single agent
[13:09] Why every fully autonomous AI agent Mike built ended badly — every single time
[13:36] The human-in-the-loop requirement: LLMs lie, degrade, and mispredict without oversight
[15:03] Why the data behind your AI matters as much as the AI itself
[16:12] The new problem nobody talks about: information isn't scarce anymore — attention is
[17:44] What format should your AI output be in? PDF, short-form, feed? Why this question matters more than you think
[18:13] Why Paul now has to schedule time to review what used to take 20 hours
[19:13] What's actually happening behind the AI curtain: workflows vs. agents explained simply
[21:37] Open source vs. proprietary models: when to use ChatGPT, Claude, Gemma, or a custom harness
[24:03] Why Mike builds every custom harness to work with multiple models — not just one
[24:36] Deep dive: how AI agents are being built specifically for the cannabis industry
[26:12] The dispensary compliance problem — and how an AI agent handles metric tracking and regulation
[27:52] From bud tender backup to inventory purchasing intelligence: what a dispensary AI stack looks like
[29:03] What does work look like in 10 years? Mike's honest answer
[31:30] Why AI can only copy — and why studying your field anyway is still the right move
[32:01] Why software developers still haven't been replaced after years of predictions
35 min
About Taxes and Exits
From the publisher's feed
Keep More of What You Built. Live a Life Worth Having. Without Sacrificing Your Joy.
This is the podcast for 7–8 figure business owners who are approaching, or have already had, an exit, and don't want to hand half of it to the IRS.
Every week, you'll hear from founders, operators, and wealth strategists who've navigated the exit, the tax bill, and the harder question on the other side: now what?
Hosted by Paul H. Graham, a 3x founder, co-author with Kevin Harrington (the Original Shark from Shark Tank), and author of The Entrepreneur's Tax Strategy. Paul has built, sold, and driven over nine figures in value across his companies. As Chief Growth Officer at Stakeholders Family Office, he helps 7–8 figure business owners coordinate tax strategy, alternative investments, and exit planning under one roof, so nothing falls through the cracks before or after the transaction.
If you're a business owner scaling toward a liquidity event, trying to protect what the sale just created, and unwilling to sacrifice your joy in the process, this show was built for you.
Subscribe for free and join the live show to ask your questions directly. When you're ready to talk about what a fractional family office could do for your situation, start at investorsguidetojoy.beehiiv.com