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Anna Simpson’s philosophy is that you don’t make money in your comfort zone. Once she has achieved a goal, Anna finds a way to push her limits and look forward to the next. And when things start to get difficult, that’s when Ana knows she needs to keep digging: She’s getting closer to the gold.

Anna is a full-time accredited multifamily investor and deal sponsor with experience in property valuation, acquisition, rehabilitation, leasing and asset management. She got her start investing in single family buy and holds before making the decision to transition to multifamily as a passive investor. Anna personally invested in 1,300 multifamily units as an equity partner and key principal before she was ready for the next challenge of becoming a managing partner. Today, Anna has completed two multifamily deals: a 70-unit syndication and a 76-unit 1031 exchange.

Today, Anna sits down with me to share her decision to work ON the business rather than IN it by making the shift to multifamily. She explains how she leveraged her role as a passive investor to learn the fundamentals of syndication and the key challenge she faced in landing her first deal as managing partner. Anna offers insight around the value of persistence and breaking big goals down into smaller chunks. Listen in for Anna’s advice on pushing beyond your perceived limits and learn why she believes that while knowledge is important, true power lies in consistent ACTION.

Key Takeaways

How Anna got involved with real estate

  • Friends active in single family group
  • ‘Success breeds success’

Anna’s initial investment strategy

  • Single family buy and hold rentals
  • Successful but difficult to scale

Anna’s shift to multifamily

  • Working on New Year’s Eve
  • Made decision to work ON vs. IN
  • Got involved as passive investor

What Ana learned as a passive investor

  • How to communicate with vendors, investors
  • How to supervise rehab
  • How to design, implement plan

Anna’s first multifamily deal

  • Found off-market through relationships
  • Syndicated 70-unit deal (23 passive investors)
  • $4M purchase price, $1.4M raise in one day

Anna’s approach to goal-setting

  • Identify where you are and where you want to be
  • Break down into smaller goals (e.g.: one LOI/week)
  • Work backwards and assess regularly

Anna’s key challenge in landing her first multifamily deal

  • Overcame lack of track record with team
  • Experience as investor in 1,300 doors

How the Law of the First Deal impacted Anna

  • Second deal under contract 2 months after first
  • Off-market deal through broker

Anna’s insight on the value of persistence

  • Difficult times mean you’re getting closer
  • Accept setbacks as part of journey
  • Move forward to build reputation, respect

What Anna would do differently given the opportunity

  • Start earlier with apartments
  • ‘You don’t know what you don’t know’

Anna’s advice for aspiring real estate investors

  • Learn through podcasts, groups, etc.
  • Treat as business not hobby
  • Consistent ACTION = POWER
  • Work on mindset constantly
  • Leverage passion on down days

How Anna navigates the down days

  • Surround with supportive, optimistic people

Connect with Anna

Anna’s Website


Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not by Robert T. Kiyosaki

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