Category Archives: Education


Owning the Crossroads in Investment Real Estate With Chad Braun (Ep. 36)


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, but entire communities.
  • There are some negative leverage real estate deals, but is that the best strategy if you want a positive cash flow.
  • What is the real estate future forecast, are we expecting another real estate cycle like in the 80s.
  • How Fifth Corner created a functional rent structure that is not directly affected by increasing property taxes.
  • And more…



Connect With Chad Braun:


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About Our Guest:

Chad started his career with Kenneth Leventhal & Co in their real estate advisory practice and has spent the past 24 years exclusively working in the commercial real estate business. He helped grow AmREIT (NYSE:AMRE) from $50 million to over $1 billion in assets when it sold to EDENS in February 2015. As CFO and COO, he was responsible for all aspects of capital formation, accounting and reporting, asset management, investor relations and human resources.



Affordable Housing: A Real ESG Investment With David Steinwedell (Ep. 35)

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 ESG. 
  • The difference between Capital A Affordable housing and Attainable housing. 
  • The 3 benefits of a fund managed by a nonprofit: transparency, substantial affordability and stability. 
  • The current rate environment leading to a period of price discovery in the real estate market. 
  • How does affordable housing operate.
  •  And more 


Connect With Henry Yoshida: 


Connect With SineCera Capital: 


About Our Guest: 

David Steinwedell, a 34-year veteran in real estate and investment and an 11-year Austinite, applies the best practices of private equity and asset management to the city’s moderate- and middle-income affordability challenges. David has worked at fund advisers, REITs and real estate investment banks, and has led teams in acquisitions, asset management, and debt and property management. He has been involved in over $15 billion in financial transactions across several REITs and high-net-worth investment funds, and was the executive director of the Urban Land Institute-Austin for four years until transitioning full time to his current role as president and CEO of Affordable Central Texas. His experience across all property types and various investment vehicles provides the background to make flexible investments and create innovative transaction structures to address Austin’s rapidly changing marketplace. David is a graduate of Hamilton College and has served on the boards of NAREIM, ULI – Austin and Atlanta, and the Tritt Foundation. He and his wife, Patty, reside in Austin and have three grown children. 



Should I Invest In Apartments? (Ep. 34)

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 multi-family and single-family space offerings.
  • And more… 


Connect With David Wylie: 


Connect With SineCera Capital: 


About Our Guest:  

David is the Founder & Managing Partner of Hilltop Residential. 

David has been in the multifamily investment business since 2000, having received national recognition for his performance in the apartment market across Texas and the United States. During his 21 years in the industry, David has been involved in over $15 billion of multifamily transactions. David’s deep relationships in the industry, as well as his extensive experience in identifying investment opportunities, are integral pieces to the Hilltop team. 

David attended The University of Texas where he studied business and Spanish and spent two semesters in Argentina developing his Spanish language communication skills and furthering his education. He is actively involved at Second Baptist Church, is an active member of NMHC (National Multifamily Housing Council),ULI (Urban Land Institute), and serves on the Regional Advisory Council with Apartment Life. 


Is Your Trustee Out of Touch? With Christopher Holtby (Ep. 33)

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 Trusts Work 
  • What to keep in mind when appointing a Trustee 
  • And more… 


Connect With Christopher Holtby: 


Connect With SineCera Capital: 


About Our Guest: 

At Wealth Advisors Trust Company, Christopher applies his business building, love of learning, operational, and wealth management expertise gained at Ernst & Young.  His role includes learning and facilitating knowledge around the trustee industry to assist those in choosing a  trust company. Christopher has co-authored two white papers, Directed Trusts Made Simple and the Trusteed IRA, and authored one published peer-reviewed paper, An Advisors Roadmap to the Trustee Industry.  From the operational side, Christopher created the trust administration process within SalesForce. He and his family are clients of the trust company as well. 

Christopher grew up in Toronto, Canada, graduated from the University of Arizona receiving a BA in Psychology with an emphasis on statistics and a minor in English Literature. He lives in Dallas with his wife and three sons and enjoys skiing, mountain biking, hiking, reading history, and watching and participating in sports with his sons. 


Real Estate in the Texas Triangle with John Anderson (Ep. 32)

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…


Connect With John Anderson: 

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About Our Guest: 

John Anderson serves as Chief Financial Officer, is a member of the Investment Committee and brings over 25 years of experience to the team. Prior to founding 35 South Capital, Mr. Anderson co-founded CJN Investments, a boutique private equity firm that invests in local businesses and real estate in the greater Houston area and throughout the state of Texas. Prior to CJN, he was the Regional Director of Development for Weingarten Realty. Mr. Anderson also previously worked at Pelican Builders, AmReit, Fairfield Residential and the Archon Group (a subsidiary of Goldman Sachs).  

John graduated from Baylor University with a BBA is Business Management and an MBA from The University of Texas at Austin, specializing in Real Estate and Investments.


The Current M&A Market: Is This the Right Time To Sell a Business? With Jack Selman (Ep. 26)

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 Jack Selman, partner at Selman Munson & Lerner P.C., about pre-liquidity planning in the current M&A landscape and how entrepreneurs can optimize their exit strategy.

Kevin and Jack discuss:

  • ”01:38” The “Great Wealth Transfer” and the rise of private equity
  • ”06:12” Biggest reasons why family businesses are motivated to sell
  • ”07:16” How to value a business (and different types of buyers to consider)
  • ”19:56” Two action steps that Jack suggests based on his past M&A transactions
  • And more


Connect With Jack Selman:

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Kitchen Table Conversations (Part 1): Key Financial Topics Every Family Should Consider (Ep. 25)

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 consider in light of current market conditions and in general.

Kevin and Connee discuss:

  • ”00:49” Using asset allocation to hedge against the risk of inflation
  • ”03:08” How donor-advised funds lead to tax-efficient philanthropy
  • ”08:14” The importance of “ document e-Vaulting” in family affairs
  • ”14:44” Key cybersecurity measures to ensure protection of financial records
  • And more

Connect With SineCera Capital:


Fund of Funds: Accessing Top-Tier Venture Capital and Growth Equity Funds With Aram Verdiyan of Accolade Partners (Ep. 24)

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 Verdiyan, partner at Accolade Partners and one of SineCera Capital’s partners, to break the stigma around fund of funds’ high-cost structure. Aram also shares his experience using concentrated capital allocations to enhance portfolio returns.

Aram discusses: 

  • ”03:30” Three compelling reasons to invest in a fund of funds
  • ”17:21” Why growth equity remains an immensely underappreciated asset class within private equity
  • ”20:29” The relevance of blockchain venture funds (with a brief overview of blockchain technology)
  • ”33:40” How the current recessionary period has impacted valuations
  • And more

Connect With Aram Verdiyan:

Connect With SineCera Capital:

About Our Guest:

Aram Verdiyan is a partner at Accolade Partners. Previously, he worked on the investment team at Andreessen Horowitz. Before that, Aram worked in BD, sales and marketing at Aviatrix, a cloud native enterprise software company. Aram worked at Accolade from 2012 to 2015 as a Senior Investment Associate and at Deloitte Consulting LLP. He holds an M.B.A from the Stanford Graduate School of Business (GSB) and a B.S. from George Washington University.


Early-Stage Venture Capital: Opportunities in Enterprise SaaS & Fintech With Anna Garcia (Ep. 23)

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 capital fund focused on B2B Fintech and Enterprise SaaS startups. Anna shares her experience in pre-seed, seed, and post-seed funding and insights into her priority investment themes in today’s environment.

Anna discusses: 

  • ”02:10” Her journey as a financial practitioner, an angel investor, and a venture capitalist
  • ”06:57” The key differences between different stages of seed investing
  • ”12:24” Advantages that smaller, newer managers have in venture capital
  • ”19:01” The impact of recession on capital flows into private equity
  • And more

Connect With Anna Garcia:

Connect With SineCera Capital:

About Our Guest:

Anna Garcia, CFA, is the founder and managing partner of Altari Ventures, a New York based venture capital fund focused on pre-seed, seed, B2B, FinTech, and enterprise SaaS. Altari Venture’s priority investment themes include data-driven business intelligence, capital markets technology, institutional asset management technology, CFO tech stack, embedded finance, and decentralized centralized infrastructure conversions.

Immediately prior to founding Altari, Anna was the general partner and co-founder of Runway Venture Partners, a post-seed B2B SaaS fund. Before venture, she spent 17 years on Wall Street in a variety of senior investment banking and asset management roles at Merrill Lynch, Jeffries and JP Morgan.

Since becoming involved in the New York startup ecosystem post financial crisis, Anna has actively leveraged her unique perspective as a financial practitioner and software investor, as well as her extensive network, to source and vet investment opportunities and support portfolio companies’ growth. Anna’s notable investments include Trumid, a FinTech unicorn, Liveoak Technologies acquired by DocuSign, Owlet, taken public in a SPAC IPO, Logiwa, YayPay acquired by Quadient, Agilis, Monit. She was recognized with a market’s choice women in finance 2017 award for excellence in FinTech and named to innovate finance women in FinTech powerless of 2018.


Venture Capital Today: Creating Alliances and Evaluating Market Segments With Steve Brotman (Ep. 22)

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 Alpha Partners and a strategic advisor to Pritzker Group Venture Capital. They talk about Steve’s experience in the venture capital space and some interesting market segments in the current economy.

Steve discusses: 

  • ”04:40” How he came to start his own growth equity firm, Alpha Partners
  • ”17:02” The major barriers to entry in the current venture capital landscape
  • ”22:54” How a potential recession and the rising cost of capital might influence venture capital moving forward
  • ”25:53” Market segments worth looking into during economic downturns
  • And more

Connect With Steve Brotman:

Connect With SineCera Capital:

About Our Guest:

Steve Brotman’s first entrepreneurial effort was when he was the co-founder of a venture-backed company known as the pioneer of online classified advertising platforms called AdOne. He started AdOne as an assignment in an entrepreneurship class at Columbia Business School and the company later signed over one third of the newspaper industry at the time.

He moved on to found Silicon Alley Venture Partners with $15 million assets under management. He later became the co-founder and Managing Director of Greenhill SAVP, a technology and business information services venture capital fund with $100 million under management.

Steve is now the founder and managing partner at Alpha Partners. He is also an entrepreneur, investor and fund manager, and serves as a Strategic Advisor to Pritzker Group Venture Capital.