2026-03-10 - Evan Shortreed

• Enterprise Managed Services Focus: Prioritize five large clients, using ongoing managed services for long-term retention without multiple vendors.

• Active LinkedIn Content Strategy: Engage clients via posts and free pre-engagement sessions, establishing trust and value before contracts.

• Pricing Strategy for Enterprise Clients: Charge $250/hour, justifying rates against full-time hire costs while supporting larger project budgets.

• Operational Resilience Services: Focus on critical security issues like backups and account access, revealing overlooked risks for deeper client trust.

• Cold Outreach Techniques: Use email scraping and personalized mail to effectively reach decision-makers avoiding digital noise.

• Long-Term Partnership Approach: Emphasize mutual growth over competition, showing value early to secure long-term client relationships.

Notes

Client Engagement and Business Development Strategy

The discussion revealed a clear approach to building long-term client relationships by focusing on enterprise-level managed services and leveraging expert networks for comprehensive solutions.

• Enterprise Managed Services Focus with High-Value Clients (04:15)

  • Evan Shortreed concentrates on large clients, having worked with five enterprise clients through short-term engagements that evolve into ongoing managed services.

  • He acts as a “quarterback,” identifying client needs and bringing in specialists like Dmitri for areas outside his expertise.

  • This approach ensures clients receive broad expertise without needing multiple vendors and promotes long-term retention.

  • Evan’s strategy is to stay proactive by learning new tech trends, such as AI, to continuously add value and retain clients over years.

• Client Acquisition via Active LinkedIn Content and Outreach (16:58)

  • Evan has posted on LinkedIn for around 30 weeks, gaining steady inbound interest with several semi-viral posts.

  • He uses free pre-engagement mapping sessions with tools like Mural and Lucidchart to visualize client processes and highlight inefficiencies.

  • This teaching approach builds trust and demonstrates value before formal contracting.

  • Cold outreach includes targeting contract job postings with offers to deliver faster results than hiring employees.

• Pricing Strategy Targeting Enterprise Budgets (20:07)

  • Evan charges $250 per hour for consulting but notes smaller companies sometimes balk at this rate.

  • He justifies pricing by comparing it favorably to employee costs, including onboarding, vacation, and benefits.

  • This pricing model supports focus on larger clients with bigger budgets and longer engagements.

  • Monthly billing is used for scoped projects, while hourly billing applies to out-of-scope work.

• Partnership and Network Building Philosophy (21:07)

  • Both Dmitri and Evan emphasize collaboration over competition, viewing partnerships as a way to multiply opportunities.

  • They share a mindset of openly sharing knowledge and connecting clients with the right experts rather than hoarding information.

  • This approach aligns with their goal of solving complex client problems and expanding their reach together.

  • They see this cooperation as essential for thriving in a crowded and evolving market.

Operational Resilience and Security Focus

Dmitri is pivoting to foundational security and operational resilience services, addressing common enterprise gaps in backup, account access, and system consolidation.

• Operational Resilience Checkup as Market Entry Wedge (12:25)

  • Dmitri’s current offering centers on basic but critical security hygiene such as password management and account access controls.

  • He highlights frequent organizational blind spots like lack of reliable backups and overreliance on third-party providers like Microsoft or Google.

  • This foundational work uncovers risks that many organizations overlook, representing a high-impact service.

  • The goal is to build trust and open doors for deeper engagements by fixing these “rocks in their shoes.”

• Challenges with Software Adoption and User Training (25:30)

  • Both agreed the biggest hurdle is ensuring proper software use, not just deployment.

  • Dmitri is seeking partners willing to provide patient, hands-on user support following SOPs to overcome adoption barriers.

  • Evan uses recorded Loom videos for training, creating a knowledge base to reduce repetitive help requests.

  • They acknowledged “train the trainer” models rarely work effectively, so direct user support is key.

• Security Innovation and Encryption Awareness (23:20)

  • Evan works with university experts developing AI and encryption wrappers to improve data security in cloud systems.

  • Dmitri noted the importance of secure key management, a critical but often overlooked part of encryption security.

  • Staying connected to academic research helps keep their solutions cutting-edge and trustworthy.

  • This technical vigilance supports their credibility when advising enterprise clients on security.

• System Consolidation and Integration Needs (13:38)

  • Dmitri and Evan discussed clients juggling a “smorgasbord” of disconnected tools, complicating operations.

  • Evan builds custom MVPs linked to client data lakes to unify fragmented systems and reduce confusion.

  • This approach allows rapid deployment while cleaning up underlying process and data inconsistencies.

  • It also positions them to scale solutions efficiently as clients mature.

Market Positioning and Niche Identification

Both participants stressed the need to find clear niches and use targeted messaging to differentiate themselves and attract ideal clients.

• Niche Focus on Supply Chain and Agencies (18:34)

  • Evan identified supply chain and agency sectors as his sweet spot, due to his understanding of product-to-consumer flows.

  • He avoids overly technical biogenetics or unfocused sectors like universities because of unclear client needs.

  • Positioning as a fractional CTO and trusted advisor in these niches helps him command premium rates.

  • Dmitri is still exploring niches for his operational resilience service and values industry input for refinement.

• Client Messaging Through Education and Process Mapping (18:14)

  • Evan’s strategy includes educating clients on why current processes are inefficient by visually mapping workflows.

  • This confronts entrenched habits and opens minds to change, increasing their willingness to invest.

  • Offering free initial process reviews lowers barriers to engagement and builds credibility.

  • Dmitri plans to leverage this tactic to attract early interest and differentiate.

• Cold Outreach and Personalized Direct Mail (29:05)

  • Dmitri intends to use email scraping for cold outreach and considers reviving personalized physical mailers.

  • He cited past success with handwritten letters yielding high close rates despite the digital shift.

  • These methods aim to break through digital noise and reach decision makers more effectively.

  • Evan supports cold outreach to contract job postings as a direct way to find immediate project opportunities.

• Long-Term Vision with Multi-Venture Strategy (30:59)

  • Dmitri shared his broader vision involving the Lasting Legacy foundation for managed wealth transfer and community creation.

  • This initiative addresses the $84 trillion wealth transfer over 25 years, aiming to prevent loss across generations.

  • The foundation would lease donated properties to community builders, generating sustained impact and revenue.

  • He is also focused on reinventing alternative education by integrating elders and AI, driven by personal experience as a father.

Technology and Product Development Approach

Their approach to technology focuses on rapid custom builds using cloud platforms, data lakes, and security-enhanced AI wrappers.

• Rapid Custom MVP Development Using Cloud Code and Data Lakes (23:20)

  • Evan builds minimum viable products within a week by combining cloud code with client data lakes like Snowflake.

  • This “wrapper” approach layers front-end interfaces over existing systems to unify fragmented tools.

  • It allows clients to continue current operations while transitioning to cleaner, integrated solutions.

  • This method provides flexibility and fast time-to-value.

• Security Enhancements Through AI and Encryption Wrappers (23:55)

  • Partnership with University of South Florida professors brings advanced encryption and AI-based security wrappers.

  • These technologies aim to protect data streams uniquely while maintaining usability.

  • Evan maintains connections with academic experts to stay ahead of security risks.

  • Dmitri emphasized the importance of key management as a core security challenge.

• Enterprise-Level System Features and Scalability (34:36)

  • Dmitri offers expertise setting up enterprise-grade systems with features like activity tracking and modification history.

  • This level of detail supports strong auditability and quick scaling for bootstrapped clients.

  • He invites Evan to collaborate on pilot projects to integrate these capabilities into custom builds.

  • This partnership would combine deep system design with agile delivery.

• Focus on Usability and Adoption Support (26:03)

  • Both agree software success depends on user adoption, not just technical deployment.

  • Dmitri looks for partners who can provide steady hand-holding through SOPs to ensure proper usage.

  • Evan’s use of Loom videos for training reduces friction and supports ongoing learning.

  • This focus on usability is critical to achieving client success and retention.

Collaboration and Partnership Dynamics

The conversation underscored the value of cooperative mindsets and complementary skill sets in growing their businesses.

• Synergistic Mindset Over Competitive Hoarding (21:18)

  • Dmitri praised Evan’s openness and collaborative approach as a refreshing alternative to typical competitive attitudes.

  • They view working together as a way to improve each other’s offerings and win bigger opportunities.

  • This mindset helps them combine strengths and better serve complex client needs.

  • They both reject the “beat you out” mentality in favor of mutual growth.

• Mutual Support in Client Engagements (34:27)

  • Dmitri invited Evan to join upcoming projects aligned with his specialty, especially on enterprise system setups.

  • Evan welcomed ongoing collaboration and knowledge sharing to broaden impact.

  • They see partnership as key to navigating multi-product client demands and complex technical challenges.

  • This ongoing dialogue opens pathways for pilot projects and cross-referrals.

• Building a Network of Trusted Experts (07:06)

  • Evan described his approach of connecting clients with trusted specialists like Dmitri to fill gaps.

  • This network-based model delivers holistic solutions without overstretching any individual consultant.

  • It also helps win larger engagements by offering clients access to a full team.

  • Dmitri’s nonprofit and security background complements Evan’s enterprise software focus well.

• Long-Term Relationship Orientation (22:16)

  • Evan emphasized the importance of showing value early to maintain client relationships over many years.

  • This approach helps transition short-term projects into managed services with recurring revenue.

  • They both prioritize learning and adapting to new technologies to stay relevant for clients.

  • This strategy builds trust and deep partnership, reducing client churn risk.

Action items

Dmitri Sunshine

• Explore niche focus areas and define target market for operational resilience services (14:04)

• Pursue cold outreach campaigns using email scraping and personalized mailers to build sales pipeline (29:18)

• Follow up with Evan for potential pilot projects and collaboration opportunities (34:30)

Evan Shortreed

• Share contacts of encryption and AI experts from University of South Florida with Dmitri (24:48)

• Continue content posting and proactive LinkedIn engagement to attract enterprise clients (17:50)

• Provide advice and co-develop future projects leveraging enterprise system setup and AI integrations with Dmitri (34:30)