Summary: In this episode, Kevin Kaylakie speaks with Chad Braun, the managing partner and co-founder of Fifth Corner. Chad shares his incredible professional journey and how the Irreplaceable Corners TM approach differentiates them in the real estate space.   Kevin and Chad discuss: How a company’s core values, and strategy can impact not just investors, … Continue reading Owning the Crossroads in Investment Real Estate With Chad Braun (Ep. 36) →

In this episode, Kevin Kaylakie speaks with David Steinwedell, founder and CEO of Affordable Central Texas. They provide a brief overview of a private sector solution to a current problem in Austin and other Texas cities, affordable housing.     Kevin and David discuss:  How a private market solution can be both beneficial to investors and … Continue reading Affordable Housing: A Real ESG Investment With David Steinwedell (Ep. 35) →

Kevin and David discuss:   Investing in Value-Add versus Core-Plus investments and risk adjusted returns. Leverage and risk. To have negative leverage or to be overleveraged? Real estate as an asset appreciation, wealth preservation, and cash flowing product. How to execute a Value-Add investment strategy. The future of real estate and real estate investing. Comparing … Continue reading Should I Invest In Apartments? (Ep. 34) →

In this episode, Kevin Kaylakie speaks with Christopher Holtby, Co-Founder and Head of Learning & Business Development of Wealth Advisors Trust Company.   Kevin and Christopher discuss:  Removal and appointment of Trustees  Trust Law and the Trust Task Force in South Dakota  4 Reasons to choose South Dakota Trust Jurisdiction  How do Directed Trusts and Delegated … Continue reading Is Your Trustee Out of Touch? With Christopher Holtby (Ep. 33) →

In this episode, Kevin Kaylakie speaks with John Anderson, Chief Financial Officer at 35South Capital.    Kevin and John discuss:  Core plus real estate assets. 35South Capital and the closing of their fund.  Negative leverage in commercial real estate.  Value-add in real estate and 35South Capital’s approach.  Real Estate Investment in the Texas Triangle. And more… … Continue reading Real Estate in the Texas Triangle with John Anderson (Ep. 32) →

In this episode, Kevin Kaylakie speaks with Connee Sullivan, Head of Family Office Service for SineCera Capital.    Kevin and Connee discuss:  Tax Preparedness: contributions to 401(k)s, HSAs, 529s, Charitable contributions to DAFs, and considering estate and gift tax planning.  Tax loss harvesting.  Planning checklist and the gathering of important documents   Strategies for liquidity management.  … Continue reading Seasonal Update at Tax Time With Kevin Kaylakie (Ep. 31) →

In this episode, Connee Sullivan speaks with Kevin Kaylakie, founder and CEO of SineCera Capital. Kevin and Connee discuss:   The meaning of SineCera  The story behind and basis of our core values  Being true fiduciaries by heart and by handshake.  Selecting business partners who exemplify our values.  And more.      Connect With SineCera Capital:  … Continue reading SineCera Capital Core Values. What Make Us Who We Are With Connee Sullivan (Ep. 30) →

The dynamics of selling a business have changed considerably over the years. Private equity firms are increasingly focused on creating synergies, and many founders are staying in the business even after the sale.   In this episode, Kevin Kaylakie speaks with Terese Everson, director at Focus Strategies Investment Banking, about the exit planning process and … Continue reading Preparing for a Business Exit With Terese Everson (Ep. 29) →

Vintage timepieces are more than watches. They are unique pieces of history. They can be passed down from one generation to the next, and they often increase in value over time. Vintage watches offer both an investment opportunity and a beautiful piece of jewelry.   In this episode, Kevin Kaylakie speaks with Jacek Kozubek, the … Continue reading Vintage Timepieces: A Market for Valuable Collectibles and Family Heirlooms With Jacek Kozubek (Ep. 28) →

In traditional forms of IRAs (individual retirement accounts), investment options are often limited to stocks, bonds, and mutual funds. However, “self-directed IRAs” enable owners to invest their retirement savings into alternative asset classes.   In this episode, Kevin Kaylakie speaks with Henry Yoshida, CFP®, founder and CEO of Rocket Dollar, Inc. They provide a brief … Continue reading Latest Trends in Retirement Plan Distributions With Henry Yoshida (Ep. 27) →

Selling a business is a significant liquidity event that requires complex planning in various areas, such as business valuation, attracting the right buyers, tax planning, and post-sale wealth management. Moreover, given the current market conditions, long-time business owners might wonder: Is the timing right to sell a business? In this episode, Kevin Kaylakie speaks with … Continue reading The Current M&A Market: Is This the Right Time To Sell a Business? With Jack Selman (Ep. 26) →

With the end of 2022 fast approaching, several financial issues are top of mind for many families, such as high inflation and year-end tax planning. In this episode, Kevin Kaylakie and Connee Sullivan join in a kitchen table conversation to address the financial topics that matter most to families. They also share best practices to … Continue reading Kitchen Table Conversations (Part 1): Key Financial Topics Every Family Should Consider (Ep. 25) →

Access to top-performing funds across venture capital and growth equity is often  limited to large institutional investors. Having built long-term relationships with these managers, Accolade Partners is able to gain access to their deals and offer high-net-worth clients  the opportunity to invest via diversified funds of funds.  In this episode, Kevin Kaylakie talks with Aram … Continue reading Fund of Funds: Accessing Top-Tier Venture Capital and Growth Equity Funds With Aram Verdiyan of Accolade Partners (Ep. 24) →

Seed-stage investing is a fascinating space where startups can offer considerable growth potential in their earliest stages. That attractiveness is further fueled by the recent upsurge in successful Enterprise SaaS and B2B Fintech startups. In this episode, Kevin Kaylakie talks with Anna Garcia, the Founder and Managing Partner of Altari Ventures, a New York–based venture … Continue reading Early-Stage Venture Capital: Opportunities in Enterprise SaaS & Fintech With Anna Garcia (Ep. 23) →

Early-stage venture capitalists (VCs) often lack the capital required to fund their pro-rata shares in subsequent financing rounds of their leading portfolio companies. That’s where Alpha Partners, instead of competing head-on against them, partners with early-stage VCs to bridge that capital gap. In this episode, Kevin Kaylakie talks with Steve Brotman, the managing partner of … Continue reading Venture Capital Today: Creating Alliances and Evaluating Market Segments With Steve Brotman (Ep. 22) →

After nurturing a family business for years, a founder may now be looking for successors who can grow it to the next level. This transfer can be within the family, to an existing employee, or to a strategic investor. In this episode, Kevin Kaylakie speaks with Gina Luna, Founding Partner of GP Capital. They provide … Continue reading Transitioning Capital Through a Value Added Partner With Gina Luna (Ep.21) →

In the world of investing and philanthropy these days, the focus is on impact. There is a generational divide on what this actually means and how to approach it. In this episode, Connee Sullivan speaks with Chelsea Toler, Founding Partner at NOVA Impact and President at Keep Families Giving Foundation. Together, they talk about implementing … Continue reading A Next Gen Perspective on Impact Investing and Philanthropy With Chelsea Toler (Ep.20) →

Have you ever considered fine art as collateral for private credit investments? The high-end art market attracts ultra-high-net-worth clients from around the world with art-secured lending becoming a globally valued asset class.  For private credit investors, it can be a great diversifier for their portfolios. In this episode, Kevin Kaylakie speaks with Alan Snyder, the … Continue reading Art-Secured Loans: A Unique Gateway to Private Credit with Alan Snyder (Ep. 19) →

As an entrepreneur or a private equity investor, you may be involved with businesses that are in their early growth stages and transitioning from “founder-led” to “professional management.” In this episode, Connee Sullivan speaks with Amanda Eisel, the CEO of Zelis, who has significant experience in private equity and working with founders. Amanda discusses how … Continue reading Addressing the Founder’s Dilemma from a Private Equity Lens with Amanda Eisel (Ep. 18) →

The private market space has been around for a long time. But recently, it has been gaining interest from family offices and high-net-worth individuals. SineCera Capital remains highly committed to finding the right private investment managers who can be trusted with clients’ capital. In this episode, Kevin Kaylakie sits down with Alexander Schoenbaum, CEO of … Continue reading Private Market Investing for Family Offices and High-Net-Worth Individuals with Alexander Schoenbaum (Ep. 17) →